# 1999–2000 FA Cup qualifying rounds

The 1999–2000 FA Cup qualifying rounds opened the 119th season of competition in England for 'The Football Association Challenge Cup' (FA Cup), the world's oldest association football single knockout competition. A total of 579 clubs participated in the competition after Manchester United, who were the winners the previous season, decided not enter.
The large number of clubs entering the tournament meant that the competition started with preliminary and four qualifying knockouts for these non-League teams. The 32 winning teams from Fourth qualifying round progressed to the First round proper, where League teams tiered at Levels 3 and 4 entered the competition.

## Calendar

| Round | Start date | Leagues entering at this round | New entries this round | Winners from previous round | Number of fixtures |
| Preliminary round | 21 August 1999 | Isthmian League Northern Premier League Southern League (except Premier divisions) | 394 | none | 197 |
| Preliminary round | 21 August 1999 | Combined Counties League Eastern Counties League Essex Senior League Hellenic League Kent League Midland Alliance North West Counties League Northern Counties East League Northern League South Western Football League Spartan South Midlands League Sussex County League United Counties League Wessex League Western League | 394 | none | 197 |
| First qualifying round | 4 September 1999 | none | 5 | 197 | 101 |
| Second qualifying round | 18 September 1999 | Isthmian League Northern Premier League Southern Football League (Premier divisions) | 67 | 101 | 84 |
| Third qualifying round | 2 October 1999 | none | none | 84 | 42 |
| Fourth qualifying round | 16 October 1999 | Football Conference | 22 | 42 | 32 |

## Preliminary round

Matches were played on weekend of Saturday 21 August 1999. A total of 394 clubs took part in this stage of the competition, 88 clubs from the four divisions at Level 7 of English football and 306 clubs from fifteen lower level leagues.
| Tie | Home team (tier) | Score | Away team (tier) |
| 1 | Shildon | 1–3 | Thornaby-On-Tees |
| 2 | Glasshoughton Welfare | 0–1 | Hebburn |
| 3 | Brandon United | 0–3 | Ossett Town (7) |
| 4 | Bradford Park Avenue (7) | 1–0 | Prescot Cables |
| 5 | Workington (7) | 1–2 | Burscough (7) |
| 6 | Garforth Town | 0–4 | Armthorpe Welfare |
| 7 | Dunston Federation Brewery | 1–0 | Maine Road |
| 8 | Atherton Collieries | 1–2 | Ramsbottom United |
| 9 | Marske United | 1–1 | Ashington |
| replay | Ashington | 1–2 | Marske United |
| 10 | Cheadle Town | 0–3 | Warrington Town |
| 11 | Morpeth Town | 2–1 | Harrogate Town (7) |
| 12 | Tow Law Town | 6–0 | Tadcaster Albion |
| 13 | Chester-le-Street Town | 1–3 | St Helens Town |
| 14 | Hallam | 1–2 | Liversedge |
| 15 | Billingham Town | 1–2 | Fleetwood Freeport |
| 16 | Farsley Celtic (7) | 1–1 | Guisborough Town |
| replay | Guisborough Town | 0–1 | Farsley Celtic (7) |
| 17 | Accrington Stanley (7) | 3–0 | Peterlee Newtown |
| 18 | Rossendale United | 2–0 | Chadderton |
| 19 | Netherfield Kendal (7) | 3–0 | Oldham Town |
| 20 | Harrogate Railway Athletic | 1–0 | Willington |
| 21 | Bootle | 0–0 | Jarrow Roofing BCA |
| replay | Jarrow Roofing BCA | 1–1 (5–4 p) | Bootle |
| 22 | Crook Town | 2–0 | Yorkshire Amateur |
| 23 | Louth United | 2–1 | Kennek Ryhope CA |
| 24 | Flixton (7) | 2–1 | Northallerton Town |
| 25 | Ashton United (7) | 2–1 | Clitheroe |
| 26 | Goole | 1–1 | Trafford (7) |
| replay | Trafford (7) | 6–3 | Goole |
| 27 | Woodley Sports | 2–1 | Ossett Albion |
| 28 | Pickering Town | 4–1 | Horden Colliery Welfare |
| 29 | Denaby United | 0–2 | Chorley (7) |
| 30 | Darwen | 0–1 | Billingham Synthonia |
| 31 | Brodsworth Miners Welfare | 1–0 | South Shields |
| 32 | Mossley | 2–1 | Atherton Laburnum Rovers |
| 33 | Parkgate | 1–5 | Eccleshill United |
| 34 | Thackley | 0–1 | Consett |
| 35 | North Ferriby United | 1–0 | Witton Albion (7) |
| 36 | Penrith | 4–0 | Shotton Comrades |
| 37 | Salford City | 2–0 | Evenwood Town |
| 38 | Radcliffe Borough (7) | 2–1 | Durham City |
| 39 | Selby Town | 0–3 | Bedlington Terriers |
| 40 | Bacup Borough | 2–2 | Sheffield |
| replay | Sheffield | 4–0 | Bacup Borough |
| 41 | Curzon Ashton | 0–1 | Brigg Town |
| 42 | Skelmersdale United | 5–2 | Whitley Bay (7) |
| 43 | Easington Colliery | 2–2 | Newcastle Blue Star |
| replay | Newcastle Blue Star | 4–0 | Easington Colliery |
| 44 | Seaham Red Star | 2–1 | West Auckland Town |
| 45 | Gretna (7) | 5–0 | Rossington Main |
| 46 | Brackley Town | 2–1 | Long Buckby |
| 47 | Stourbridge (7) | 3–1 | Bromsgrove Rovers (7) |
| 48 | Blackstones | 0–0 | Willenhall Town |
| replay | Willenhall Town | 4–2 | Blackstones |
| 49 | Rocester (7) | 2–3 | Spalding United (7) |
| 50 | Stamford (7) | 3–1 | Corby Town (7) |
| 51 | Belper Town (7) | 2–2 | Stourport Swifts |
| replay | Stourport Swifts | 1–2 | Belper Town (7) |
| 52 | Boston Town | 1–0 | Boldmere St Michaels |
| 53 | Stratford Town | 4–1 | Leek CSOB |
| 54 | Borrowash Victoria | 0–1 | Sutton Coldfield Town (7) |
| 55 | Matlock Town (7) | 1–0 | Chasetown |
| 56 | Moor Green (7) | 3–0 | Paget Rangers (7) |
| 57 | Barwell | 1–1 | Staveley Miners Welfare |
| replay | Staveley Miners Welfare | 5–3 | Barwell |
| 58 | Redditch United (7) | 1–0 | Kings Norton Town |
| 59 | Stafford Rangers (7) | 2–0 | Glossop North End |
| 60 | Lincoln United (7) | 1–2 | Mickleover Sports |
| 61 | Alfreton Town | 1–2 | Congleton Town (7) |
| 62 | Ford Sports Daventry | 1–2 | Nantwich Town |
| 63 | Racing Club Warwick (7) | 1–2 | Blakenall (7) |
| 64 | Shepshed Dynamo (7) | 0–3 | Raunds Town (7) |
| 65 | Bilston Town (7) | 2–4 | Oadby Town |
| 66 | Wednesfield | 1–6 | Oldbury United |
| 67 | Desborough Town | 2–3 | Northampton Spencer |
| 68 | Glapwell | 3–1 | Stapenhill |
| 69 | Bridgnorth Town | 1–3 | Hinckley United (7) |
| 70 | Wellingborough Town | 3–0 | Kidsgrove Athletic |
| 71 | Gresley Rovers (7) | 0–1 | Eastwood Town (7) |
| 72 | Holbeach United | 2–0 | Pelsall Villa |
| 73 | Newcastle Town | 1–0 | Sandwell Borough |
| 74 | VS Rugby (7) | 1–2 | Solihull Borough (7) |
| 75 | Bourne Town | 0–2 | Stewarts & Lloyds Corby |
| 76 | Knypersley Victoria | 0–2 | Bedworth United (7) |
| 77 | Shifnal Town | 3–3 | Rushall Olympic |
| replay | Rushall Olympic | 0–1 | Shifnal Town |
| 78 | Arnold Town | 1–1 | Yaxley |
| replay | Yaxley | 1–2 | Arnold Town |
| 79 | Halesowen Harriers | 4–0 | West Midlands Police |
| 80 | St Neots Town | 2–1 | Hornchurch |
| 81 | Potters Bar Town | 3–3 | Flackwell Heath |
| replay | Flackwell Heath | 1–0 | Potters Bar Town |
| 82 | Great Wakering Rovers | 0–0 | Staines Town (7) |
| replay | Staines Town (7) | 5–0 | Great Wakering Rovers |
| 83 | Chalfont St Peter | 0–6 | Barking |
| 84 | Stotfold | 0–0 | Wembley |
| replay | Wembley | 2–1 | Stotfold |
| 85 | Grays Athletic (7) | 7–1 | Basildon United |
| 86 | Diss Town | 1–6 | AFC Sudbury |
| 87 | Ely City | 2–3 | Witham Town |
| 88 | Berkhamsted Town | 2–2 | Bishop's Stortford (7) |
| replay | Bishop's Stortford (7) | 3–3 (4–2 p) | Berkhamsted Town |
| 89 | Tiptree United | 2–0 | London Colney |
| 90 | Wealdstone (7) | 1–0 | Clacton Town |
| 91 | Fakenham Town | 3–2 | Brook House |
| 92 | Southend Manor | 4–0 | Ilford |
| 93 | Southall | 2–5 | Witney Town (7) |
| 94 | Felixstowe Port & Town | 1–3 | Wingate & Finchley |
| 95 | Watton United | 0–1 | Arlesey Town |
| 96 | Saffron Walden Town | 5–0 | Kempston Rovers |
| 97 | Romford (7) | 1–0 | Maldon Town |
| 98 | Burnham (7) | 0–1 | Wisbech Town (7) |
| 99 | Harwich & Parkeston | 2–3 | Harlow Town (7) |
| 100 | Warboys Town | 3–3 | Bury Town |
| replay | Bury Town | 2–2 (3–4 p) | Warboys Town |
| Tie | Home team (tier) | Score | Away team (tier) |
| 101 | Concord Rangers | 2–2 | East Thurrock United |
| replay | East Thurrock United | 4–2 | Concord Rangers |
| 102 | Uxbridge (7) | 0–1 | Wroxham |
| 103 | Ruislip Manor | 2–0 | Leighton Town |
| 104 | Gorleston | 1–1 | Lowestoft Town |
| replay | Lowestoft Town | 1–2 | Gorleston |
| 105 | Wivenhoe Town | 0–1 | Bedford Town (7) |
| 106 | Banbury United | 2–0 | Milton Keynes City |
| 107 | Burnham Ramblers | 1–2 | Hoddesdon Town |
| 108 | Great Yarmouth Town | 5–3 | Tilbury |
| 109 | Braintree Town (7) | 1–1 | Leyton Pennant (7) |
| replay | Leyton Pennant (7) | 1–2 | Braintree Town (7) |
| 110 | Hemel Hempstead Town | 4–0 | Harpenden Town |
| 111 | Soham Town Rangers | 7–0 | Buckingham Town |
| 112 | Aveley | 1–0 | Stansted |
| 113 | Histon | 1–0 | Hullbridge Sports |
| 114 | Wootton Blue Cross | 0–2 | Cheshunt |
| 115 | Waltham Abbey | 1–1 | Yeading (7) |
| replay | Yeading (7) | 1–3 | Waltham Abbey |
| 116 | Ware | 3–0 | Newmarket Town |
| 117 | Stowmarket Town | 3–0 | Welwyn Garden City |
| 118 | Baldock Town (7) | 6–0 | Potton United |
| 119 | Bowers United | 4–0 | Hanwell Town |
| 120 | Ford United | 5–1 | Edgware Town |
| 121 | Woodbridge Town | 1–5 | Chelmsford City (7) |
| 122 | Halstead Town | 1–3 | Royston Town |
| 123 | Beaconsfield SYCOB | 3–0 | Eynesbury Rovers |
| 124 | Hertford Town | w/o | Barkingside |
| Walkover for Hertford Town – Barkingside removed ||||
| 125 | Northwood | 8–0 | Clapton |
| 126 | Marlow | 2–2 | Barton Rovers (7) |
| replay | Barton Rovers (7) | 1–3 | Marlow |
| 127 | Kingsbury Town | 2–1 | Tring Town |
| 128 | East Cowes Victoria Athletic | 0–1 | Sittingbourne (7) |
| 129 | Folkestone Invicta (7) | 4–2 | Croydon Athletic |
| 130 | Bracknell Town | 2–2 | Camberley Town |
| replay | Camberley Town | 1–3 | Bracknell Town |
| 131 | Cobham | 1–1 | Farnham Town |
| replay | Farnham Town | 3–2 | Cobham |
| 132 | Ashford Town (Middx) | 1–2 | Langney Sports |
| 133 | Saltdean United | 1–0 | Beckenham Town |
| 134 | Eastbourne Town | 0–0 | Three Bridges |
| replay | Three Bridges | 1–1 (3–4 p) | Eastbourne Town |
| 135 | Ash United | 1–2 | Chatham Town |
| 136 | Newport (Isle of Wight) (7) | 2–0 | North Leigh |
| 137 | Erith & Belvedere (7) | 0–2 | Wick |
| 138 | Abingdon Town | 6–0 | Peacehaven & Telscombe |
| 139 | Thamesmead Town | 2–2 | Reading Town |
| replay | Reading Town | 1–0 | Thamesmead Town |
| 140 | Chipstead | 0–5 | Tonbridge Angels (7) |
| 141 | Hillingdon Borough | 1–1 | St Leonards (7) |
| replay | St Leonards (7) | 4–1 | Hillingdon Borough |
| 142 | Leatherhead (7) | 0–1 | Cowes Sports |
| 143 | Merstham | 1–5 | Corinthian-Casuals |
| 144 | Hailsham Town | 5–1 | Littlehampton Town |
| 145 | Molesey | 3–1 | Ringmer |
| 146 | Bedfont | 4–0 | Tunbridge Wells |
| 147 | Raynes Park Vale | 1–2 | Fisher Athletic (7) |
| 148 | Viking Greenford | 3–2 | Whitstable Town |
| 149 | Erith Town | 0–0 | Dorking |
| replay | Dorking | 1–2 | Erith Town |
| 150 | Ashford Town (Kent) (7) | 2–1 | East Preston |
| 151 | Shoreham | 1–2 | Abingdon United |
| 152 | Windsor & Eton | 0–0 | Bromley (7) |
| replay | Bromley (7) | 3–0 | Windsor & Eton |
| 153 | Oxford City (7) | 5–1 | Gosport Borough |
| 154 | Herne Bay | 1–0 | Canterbury City |
| 155 | Epsom & Ewell | 0–3 | Worthing (7) |
| 156 | Redhill | 2–0 | Slade Green |
| 157 | Deal Town | 5–0 | Greenwich Borough |
| 158 | Fleet Town (7) | 1–3 | Lewes |
| 159 | Hastings Town (7) | 6–1 | Southwick |
| 160 | Bognor Regis Town (7) | 2–1 | Didcot Town |
| 161 | Sandhurst Town | 0–0 | AFC Newbury |
| replay | AFC Newbury | 5–2 | Sandhurst Town |
| 162 | Thatcham Town | 4–2 | Lordswood |
| 163 | Chichester City | 2–2 | Selsey |
| replay | Selsey | 4–2 | Chichester City |
| 164 | Wokingham Town | 1–4 | Sheppey United |
| 165 | Cray Wanderers | 2–2 | Portfield |
| replay | Portfield | 2–3 | Cray Wanderers |
| 166 | Whyteleafe (7) | 4–3 | Lancing |
| 167 | Whitehawk | 0–1 | Maidenhead United (7) |
| 168 | Egham Town | 0–2 | Croydon (7) |
| 169 | Metropolitan Police | 2–1 | Chertsey Town (7) |
| 170 | Horsham | 0–1 | Hassocks |
| 171 | Fareham Town | 0–1 | Carterton Town |
| 172 | Godalming & Guildford | 1–2 | Horsham YMCA |
| 173 | Hythe United | 0–0 | Burgess Hill Town |
| replay | Burgess Hill Town | 3–0 | Hythe United |
| 174 | Arundel | 1–2 | Portsmouth Royal Navy |
| 175 | Banstead Athletic | 0–2 | Thame United (7) |
| 176 | Ramsgate | 2–1 | Dartford (7) |
| 177 | Christchurch | 1–1 | Bridport |
| replay | Bridport | 2–4 | Christchurch |
| 178 | Frome Town | 0–4 | Cinderford Town (7) |
| 179 | Mangotsfield United | 3–0 | Hungerford Town |
| 180 | Falmouth Town | 1–2 | Bideford |
| 181 | Bridgwater Town | 0–5 | Lymington & New Milton |
| 182 | Minehead Town | 1–3 | Elmore |
| 183 | AFC Totton | 1–2 | Weston-super-Mare (7) |
| 184 | Bashley (7) | 6–1 | Calne Town |
| 185 | Chippenham Town | 1–0 | Bournemouth |
| 186 | Street | 0–1 | Eastleigh |
| 187 | Welton Rovers | 4–0 | Warminster Town |
| 188 | Yate Town (7) | 0–3 | Taunton Town |
| 189 | Tiverton Town (7) | 7–1 | Pershore Town |
| 190 | Bemerton Heath Harlequins | 0–1 | Brislington |
| 191 | Melksham Town | 1–3 | Evesham United (7) |
| 192 | Downton | 3–6 | Barnstaple Town |
| 193 | St Blazey | 3–1 | Brockenhurst |
| 194 | Backwell United | 5–1 | Andover |
| 195 | Westbury United | 0–1 | Devizes Town |
| 196 | Paulton Rovers | 1–2 | Odd Down |
| 197 | Cirencester Town (7) | 3–0 | BAT Sports |

## First qualifying round

Matches were played on weekend of 4 September 1999. A total of 202 clubs took part in this stage of the competition, including the 197 winners from the preliminary round and five clubs, who get a bye to this round:
* Stocksbridge Park Steels
* Tooting & Mitcham United
* Torrington
* Tuffley Rovers
* Wimborne Town
| Tie | Home team (tier) | Score | Away team (tier) |
| 1 | Crook Town | 5–0 | Armthorpe Welfare |
| 2 | Rossendale United | 1–1 | Ossett Town (7) |
| replay | Ossett Town (7) | 2–0 | Rossendale United |
| 3 | Consett | 0–2 | Accrington Stanley (7) |
| 4 | Liversedge | 3–2 | Woodley Sports |
| 5 | Bradford Park Avenue (7) | 2–1 | Skelmersdale United |
| 6 | Thornaby-On-Tees | 1–5 | Tow Law Town |
| 7 | Brigg Town | 4–0 | Harrogate Railway Athletic |
| 8 | St Helens Town | 1–1 | Pickering Town |
| replay | Pickering Town | 3–2 | St Helens Town |
| 9 | Trafford (7) | 3–3 | Jarrow Roofing BCA |
| replay | Jarrow Roofing BCA | 1–3 | Trafford (7) |
| 10 | Hebburn | 2–2 | Louth United |
| replay | Louth United | 4–2 | Hebburn |
| 11 | Ramsbottom United | 1–2 | Fleetwood Freeport |
| 12 | Farsley Celtic (7) | 1–1 | Burscough (7) |
| replay | Burscough (7) | 0–3 | Farsley Celtic (7) |
| 13 | Mossley | 0–2 | Gretna (7) |
| 14 | Eccleshill United | 4–0 | Marske United |
| 15 | Ashton United (7) | 2–0 | Flixton (7) |
| 16 | Radcliffe Borough (7) | 8–1 | Warrington Town |
| 17 | Chorley (7) | 3–0 | Seaham Red Star |
| 18 | Penrith | 0–2 | Morpeth Town |
| 19 | Sheffield | 1–0 | Brodsworth Miners Welfare |
| 20 | North Ferriby United | 3–2 | Netherfield Kendal (7) |
| 21 | Newcastle Blue Star | 1–1 | Billingham Synthonia |
| replay | Billingham Synthonia | 3–2 | Newcastle Blue Star |
| 22 | Dunston Federation Brewery | 1–0 | Salford City |
| 23 | Bedlington Terriers | 2–0 | Stocksbridge Park Steels (7) |
| 24 | Stourbridge (7) | 0–2 | Belper Town (7) |
| 25 | Stafford Rangers (7) | 2–2 | Matlock Town (7) |
| replay | Matlock Town (7) | 0–4 | Stafford Rangers (7) |
| 26 | Northampton Spencer | 1–1 | Boston Town |
| replay | Boston Town | 4–6 | Northampton Spencer |
| 27 | Hinckley United (7) | 1–0 | Glapwell |
| 28 | Solihull Borough (7) | 1–0 | Sutton Coldfield Town (7) |
| 29 | Wellingborough Town | 2–2 | Newcastle Town |
| replay | Newcastle Town | 0–4 | Wellingborough Town |
| 30 | Oldbury United | 2–0 | Stratford Town |
| 31 | Willenhall Town | 1–1 | Oadby Town |
| replay | Oadby Town | 3–1 | Willenhall Town |
| 32 | Stamford (7) | 3–1 | Brackley Town |
| 33 | Shifnal Town | 2–3 | Congleton Town (7) |
| 34 | Bedworth United (7) | 1–3 | Redditch United (7) |
| 35 | Moor Green (7) | 3–2 | Mickleover Sports |
| 36 | Staveley Miners Welfare | 1–3 | Blakenall (7) |
| 37 | Eastwood Town (7) | 3–0 | Holbeach United |
| 38 | Halesowen Harriers | 1–4 | Arnold Town |
| 39 | Nantwich Town | 3–0 | Stewarts & Lloyds Corby |
| 40 | Spalding United (7) | 1–0 | Raunds Town (7) |
| 41 | Bishop's Stortford (7) | 4–2 | Hemel Hempstead Town |
| 42 | Banbury United | 6–3 | Gorleston |
| 43 | Cheshunt | 1–0 | Waltham Abbey |
| 44 | Wingate & Finchley | 3–2 | Braintree Town (7) |
| 45 | Great Yarmouth Town | 2–3 | Warboys Town |
| 46 | East Thurrock United | 1–2 | Baldock Town (7) |
| 47 | Romford (7) | 4–1 | Southend Manor |
| 48 | Fakenham Town | 1–3 | Staines Town (7) |
| 49 | Saffron Walden Town | 3–2 | Hoddesdon Town |
| 50 | Wisbech Town (7) | 3–1 | Wroxham |
| Tie | Home team (tier) | Score | Away team (tier) |
| 51 | Ruislip Manor | 0–1 | Beaconsfield SYCOB |
| 52 | Barking | 0–1 | Grays Athletic (7) |
| 53 | AFC Sudbury | 1–0 | Flackwell Heath |
| 54 | Hertford Town | 0–2 | Royston Town |
| 55 | Arlesey Town | 4–1 | Bowers United |
| 56 | Wealdstone (7) | 1–1 | Ford United |
| replay | Ford United | 2–3 | Wealdstone (7) |
| 57 | Marlow | 7–0 | Histon |
| 58 | Kingsbury Town | 0–1 | Chelmsford City (7) |
| 59 | Tiptree United | 1–2 | Witney Town (7) |
| 60 | Ware | 1–1 | Soham Town Rangers |
| replay | Soham Town Rangers | 2–1 | Ware |
| 61 | Wembley | 3–1 | Harlow Town (7) |
| 62 | Bedford Town (7) | 0–0 | Aveley |
| replay | Aveley | 1–2 | Bedford Town (7) |
| 63 | Northwood | 2–0 | Stowmarket Town |
| 64 | St Neots Town | 0–4 | Witham Town |
| 65 | Ashford Town (Kent) (7) | 0–2 | Fisher Athletic (7) |
| 66 | Farnham Town | 3–0 | Selsey |
| 67 | Hailsham Town | 1–3 | Sittingbourne (7) |
| 68 | Bedfont | 5–1 | Reading Town |
| 69 | Worthing (7) | 2–1 | Saltdean United |
| 70 | Maidenhead United (7) | 5–0 | Viking Greenford |
| 71 | Horsham YMCA | 3–0 | Cray Wanderers |
| 72 | Folkestone Invicta (7) | 1–3 | Ramsgate |
| 73 | St Leonards (7) | 0–1 | Bognor Regis Town (7) |
| 74 | Eastbourne Town | 0–4 | Langney Sports |
| 75 | Lewes | 3–3 | Erith Town |
| replay | Erith Town | 3–4 | Lewes |
| 76 | Tonbridge Angels (7) | 3–0 | Abingdon Town |
| 77 | Molesey | 0–3 | Hastings Town (7) |
| 78 | Thame United (7) | 3–1 | Wick |
| 79 | Abingdon United | 0–6 | Oxford City (7) |
| 80 | Deal Town | 2–0 | Metropolitan Police |
| 81 | Thatcham Town | 4–6 | Cowes Sports |
| 82 | Carterton Town | 1–4 | Herne Bay |
| 83 | Corinthian-Casuals | 4–0 | Sheppey United |
| 84 | Hassocks | 1–1 | Bromley (7) |
| replay | Bromley (7) | 2–1 | Hassocks |
| 85 | Redhill | 1–1 | Burgess Hill Town |
| replay | Burgess Hill Town | 3–0 | Redhill |
| 86 | AFC Newbury | 3–1 | Portsmouth Royal Navy |
| 87 | Chatham Town | 2–3 | Newport (Isle of Wight) (7) |
| 88 | Croydon (7) | 1–3 | Whyteleafe (7) |
| 89 | Bracknell Town | 2–4 | Tooting & Mitcham United |
| 90 | Elmore | 0–3 | Welton Rovers |
| 91 | Lymington & New Milton | 3–0 | Bideford |
| 92 | Devizes Town | 0–2 | Weston-super-Mare (7) |
| 93 | Mangotsfield United | 1–1 | Odd Down |
| replay | Odd Down | 1–2 | Mangotsfield United |
| 94 | Backwell United | 5–0 | Bashley (7) |
| 95 | Cinderford Town (7) | 0–1 | Barnstaple Town |
| 96 | Tiverton Town (7) | 4–3 | Evesham United (7) |
| 97 | Christchurch | 1–0 | Brislington |
| 98 | Cirencester Town (7) | 2–2 | Taunton Town |
| replay | Taunton Town | 4–0 | Cirencester Town (7) |
| 99 | Torrington | 0–2 | Wimborne Town |
| 100 | Chippenham Town | 2–1 | St Blazey |
| 101 | Tuffley Rovers | 2–1 | Eastleigh |

## Second qualifying round

Matches were played on weekend of 18 September 1999. A total of 168 clubs took part in this stage of the competition, including the 101 winners from the first qualifying round and 67 Level 6 clubs, from Premier divisions of the Isthmian League, Northern Premier League and Southern Football League, entering at this stage.
| Tie | Home team (tier) | Score | Away team (tier) |
| 1 | Guiseley (6) | 6–0 | Pickering Town |
| 2 | Gateshead (6) | 3–0 | Winsford United (6) |
| 3 | Ossett Town (7) | 2–1 | Spennymoor United (6) |
| 4 | Morpeth Town | 2–1 | Tow Law Town |
| 5 | Worksop Town (6) | 2–3 | Bishop Auckland (6) |
| 6 | Lancaster City (6) | Bye | Fleetwood Freeport |
| Match cancelled - Fleetwood Freeport expelled for fielding ineligible player in Preliminary round ||||
| 7 | Gainsborough Trinity (6) | 2–0 | Eccleshill United |
| 8 | Leigh RMI (6) | 5–3 | Blyth Spartans (6) |
| 9 | Hyde United (6) | 1–1 | Crook Town |
| replay | Crook Town | 2–1 | Hyde United (6) |
| 10 | Barrow (6) | 2–2 | Marine (6) |
| replay | Marine (6) | 3–2 | Barrow (6) |
| 11 | Ashton United (7) | 0–2 | Brigg Town |
| 12 | Accrington Stanley (7) | 0–2 | Whitby Town (6) |
| 13 | Trafford (7) | 2–2 | Bamber Bridge (6) |
| replay | Bamber Bridge (6) | 2–1 | Trafford (7) |
| 14 | Billingham Synthonia | 1–2 | North Ferriby United |
| 15 | Liversedge | 1–2 | Dunston Federation Brewery |
| 16 | Stalybridge Celtic (6) | 1–0 | Colwyn Bay (6) |
| 17 | Emley (6) | 2–0 | Louth United |
| 18 | Sheffield | 0–0 | Farsley Celtic (7) |
| replay | Farsley Celtic (7) | 2–1 | Sheffield |
| 19 | Runcorn (6) | 2–0 | Gretna (7) |
| 20 | Bradford Park Avenue (7) | 2–2 | Droylsden (6) |
| replay | Droylsden (6) | 2–1 | Bradford Park Avenue (7) |
| 21 | Radcliffe Borough (7) | 0–1 | Chorley (7) |
| 22 | Frickley Athletic (6) | 0–1 | Bedlington Terriers |
| 23 | Nantwich Town | 1–0 | Hucknall Town (6) |
| 24 | Solihull Borough (7) | 3–4 | Ilkeston Town (6) |
| 25 | Moor Green (7) | 2–1 | Atherstone United (6) |
| 26 | Redditch United (7) | 0–1 | Burton Albion (6) |
| 27 | Tamworth (6) | 6–1 | Spalding United (7) |
| 28 | Boston United (6) | 3–1 | Oldbury United |
| 29 | Oadby Town | 2–1 | Halesowen Town (6) |
| 30 | Leek Town (6) | 0–2 | Blakenall (7) |
| 31 | Belper Town (7) | 4–2 | Arnold Town |
| 32 | Grantham Town (6) | 6–0 | Northampton Spencer |
| 33 | Hinckley United (7) | 2–0 | Wellingborough Town |
| 34 | Stamford (7) | 1–1 | Congleton Town (7) |
| replay | Congleton Town (7) | 2–0 | Stamford (7) |
| 35 | Stafford Rangers (7) | 1–3 | Eastwood Town (7) |
| 36 | Wisbech Town (7) | 1–3 | Billericay Town (6) |
| 37 | Bishop's Stortford (7) | 1–1 | Wingate & Finchley |
| replay | Wingate & Finchley | 3–2 | Bishop's Stortford (7) |
| 38 | Warboys Town | 0–2 | Witney Town (7) |
| 39 | AFC Sudbury | 1–2 | Dagenham & Redbridge (6) |
| 40 | Canvey Island (6) | 3–1 | Boreham Wood (6) |
| 41 | Heybridge Swifts (6) | 1–2 | Romford (7) |
| 42 | Purfleet (6) | 0–0 | Banbury United |
| replay | Banbury United | 0–1 | Purfleet (6) |
| 43 | Northwood | 3–3 | Rothwell Town (6) |
| replay | Rothwell Town (6) | 2–0 | Northwood |
| 44 | Cambridge City (6) | 3–1 | Arlesey Town |
| 45 | Beaconsfield SYCOB | 0–3 | King's Lynn (6) |
| Tie | Home team (tier) | Score | Away team (tier) |
| 46 | Saffron Walden Town | 1–4 | Hitchin Town (6) |
| 47 | Aylesbury United (6) | 1–3 | Chelmsford City (7) |
| 48 | Bedford Town (7) | 0–2 | St Albans City (6) |
| 49 | Chesham United (6) | 1–3 | Baldock Town (7) |
| 50 | Royston Town | 1–3 | Wembley |
| 51 | Soham Town Rangers | 1–3 | Enfield (6) |
| 52 | Staines Town (7) | 0–3 | Wealdstone (7) |
| 53 | Marlow | 1–4 | Harrow Borough (6) |
| 54 | Hendon (6) | 2–0 | Grays Athletic (7) |
| 55 | Cheshunt | 0–0 | Witham Town |
| replay | Witham Town | 0–2 | Cheshunt |
| 56 | Aldershot Town (6) | 6–1 | Lewes |
| 57 | Thame United (7) | 0–1 | Whyteleafe (7) |
| 58 | Hampton & Richmond Borough (6) | 1–1 | Bognor Regis Town (7) |
| replay | Bognor Regis Town (7) | 0–0 (5–4 p) | Hampton & Richmond Borough (6) |
| 59 | Ramsgate | 0–3 | Margate (6) |
| 60 | Burgess Hill Town | 2–2 | Bedfont |
| replay | Bedfont | 0–2 | Burgess Hill Town |
| 61 | Walton & Hersham (6) | 0–2 | Maidenhead United (7) |
| 62 | Tooting & Mitcham United | 0–2 | Oxford City (7) |
| 63 | Farnham Town | 2–2 | Herne Bay |
| replay | Herne Bay | X | Farnham Town |
| The final result was 1-1 after extra time, with Herne Bay winning the penalty shoot-out 4-3, but the entire match was declared void when a rule break was discovered, enforcing a second replay ||||
| 2nd replay | Farnham Town | 1–2 | Herne Bay |
| 64 | Hastings Town (7) | 3–1 | AFC Newbury |
| 65 | Carshalton Athletic (6) | 2–2 | Sittingbourne (7) |
| replay | Sittingbourne (7) | 0–1 | Carshalton Athletic (6) |
| 66 | Tonbridge Angels (7) | 0–2 | Farnborough Town (6) |
| 67 | Horsham YMCA | 4–0 | Corinthian-Casuals |
| 68 | Newport (Isle of Wight) (7) | 1–1 | Dulwich Hamlet (6) |
| replay | Dulwich Hamlet (6) | 4–1 | Newport (Isle of Wight) (7) |
| 69 | Slough Town (6) | 3–1 | Cowes Sports |
| 70 | Havant & Waterlooville (6) | 2–2 | Langney Sports |
| replay | Langney Sports | 2–1 | Havant & Waterlooville (6) |
| 71 | Bromley (7) | 4–1 | Crawley Town (6) |
| 72 | Gravesend & Northfleet (6) | 1–1 | Fisher Athletic (7) |
| replay | Fisher Athletic (7) | 2–1 | Gravesend & Northfleet (6) |
| 73 | Deal Town | 2–2 | Worthing (7) |
| replay | Worthing (7) | 3–0 | Deal Town |
| 74 | Christchurch | 2–3 | Worcester City (6) |
| 75 | Clevedon Town (6) | 2–1 | Tiverton Town (7) |
| 76 | Taunton Town | 3–0 | Dorchester Town (6) |
| 77 | Newport County (6) | 1–1 | Wimborne Town |
| replay | Wimborne Town | 0–3 | Newport County (6) |
| 78 | Barnstaple Town | 2–3 | Backwell United |
| 79 | Weymouth (6) | 0–0 | Gloucester City (6) |
| replay | Gloucester City (6) | 2–1 | Weymouth (6) |
| 80 | Bath City (6) | 4–0 | Weston-super-Mare (7) |
| 81 | Lymington & New Milton | 1–1 | Tuffley Rovers |
| replay | Tuffley Rovers | 0–5 | Lymington & New Milton |
| 82 | Welton Rovers | 1–3 | Salisbury City (6) |
| 83 | Chippenham Town | 2–0 | Mangotsfield United |
| 84 | Basingstoke Town (6) | 0–0 | Merthyr Tydfil (6) |
| replay | Merthyr Tydfil (6) | 2–1 | Basingstoke Town (6) |

## Third qualifying round

Matches were played on weekend of 2 October 1999. A total of 84 clubs took part, all having progressed from the second qualifying round.
| Tie | Home team (tier) | Score | Away team (tier) |
| 1 | Dunston Federation Brewery | 0–2 | Runcorn (6) |
| 2 | Bamber Bridge (6) | 3–0 | Morpeth Town |
| 3 | Stalybridge Celtic (6) | 4–2 | Farsley Celtic (7) |
| 4 | Bishop Auckland (6) | 1–1 | Bedlington Terriers |
| replay | Bedlington Terriers | 0–1 | Bishop Auckland (6) |
| 5 | Lancaster City (6) | 2–2 | Whitby Town (6) |
| replay | Whitby Town (6) | 2–2 (2–4 p) | Lancaster City (6) |
| 6 | Marine (6) | 2–0 | Chorley (7) |
| 7 | North Ferriby United | 1–3 | Guiseley (6) |
| 8 | Droylsden (6) | 2–2 | Gainsborough Trinity (6) |
| replay | Gainsborough Trinity (6) | 1–2 | Droylsden (6) |
| 9 | Leigh RMI (6) | 1–1 | Crook Town |
| replay | Crook Town | 2–1 | Leigh RMI (6) |
| 10 | Gateshead (6) | 4–0 | Brigg Town |
| 11 | Ossett Town (7) | 0–0 | Emley (6) |
| replay | Emley (6) | 4–1 | Ossett Town (7) |
| 12 | Enfield (6) | 2–0 | Billericay Town (6) |
| 13 | Wembley | 0–3 | Canvey Island (6) |
| 14 | Chelmsford City (7) | 1–0 | Moor Green (7) |
| 15 | Belper Town (7) | 1–2 | Tamworth (6) |
| 16 | Wingate & Finchley | 0–5 | Ilkeston Town (6) |
| 17 | Hitchin Town (6) | 2–1 | Grantham Town (6) |
| 18 | Eastwood Town (7) | 3–0 | Oadby Town |
| 19 | Romford (7) | 6–0 | Congleton Town (7) |
| 20 | Cambridge City (6) | 1–0 | King's Lynn (6) |
| Tie | Home team (tier) | Score | Away team (tier) |
| 21 | Baldock Town (7) | 5–1 | Cheshunt |
| 22 | Wealdstone (7) | 1–1 | Rothwell Town (6) |
| replay | Rothwell Town (6) | 2–0 | Wealdstone (7) |
| 23 | Dagenham & Redbridge (6) | 0–2 | Burton Albion (6) |
| 24 | St Albans City (6) | 4–2 | Nantwich Town |
| 25 | Hendon (6) | 2–1 | Blakenall (7) |
| 26 | Boston United (6) | 4–0 | Purfleet (6) |
| 27 | Witney Town (7) | 2–1 | Hinckley United (7) |
| 28 | Chippenham Town | 1–1 | Worthing (7) |
| replay | Worthing (7) | 3–1 | Chippenham Town |
| 29 | Dulwich Hamlet (6) | 2–1 | Hastings Town (7) |
| 30 | Bath City (6) | 3–1 | Farnborough Town (6) |
| 31 | Maidenhead United (7) | 0–1 | Salisbury City (6) |
| 32 | Gloucester City (6) | 2–3 | Merthyr Tydfil (6) |
| 33 | Whyteleafe (7) | 1–0 | Langney Sports |
| 34 | Backwell United | 2–4 | Oxford City (7) |
| 35 | Bognor Regis Town (7) | 1–0 | Bromley (7) |
| 36 | Fisher Athletic (7) | 1–2 | Aldershot Town (6) |
| 37 | Herne Bay | 0–3 | Horsham YMCA |
| 38 | Worcester City (6) | 3–2 | Harrow Borough (6) |
| 39 | Slough Town (6) | 1–0 | Carshalton Athletic (6) |
| 40 | Newport County (6) | 1–2 | Burgess Hill Town |
| 41 | Lymington & New Milton | 3–1 | Clevedon Town (6) |
| 42 | Taunton Town | 0–3 | Margate (6) |

## Fourth qualifying round

Matches were played on weekend of Saturday 16 October 1999. A total of 64 clubs took part, 42 having progressed from the third qualifying round and 22 clubs from Football Conference, forming Level 5 of English football, entering at this stage. The round featured Burgess Hill Town and Horsham YMCA from the Sussex County Football League, Crook Town from the Northern Football League and Lymington & New Milton from the Wessex Football League still in the competition, being the lowest ranked clubs in this round.
| Tie | Home team (tier) | Score | Away team (tier) |
| 1 | Nuneaton Borough (5) | 2–3 | Guiseley (6) |
| 2 | Droylsden (6) | 0–2 | Eastwood Town (7) |
| 3 | Telford United (5) | 0–0 | Gateshead (6) |
| replay | Gateshead (6) | 2–1 | Telford United (5) |
| 4 | Scarborough (5) | 0–1 | Tamworth (6) |
| 5 | Doncaster Rovers (5) | 7–0 | Crook Town |
| 6 | Southport (5) | 1–1 | Emley (6) |
| replay | Emley (6) | 0–2 | Southport (5) |
| 7 | Northwich Victoria (5) | 2–2 | Hednesford Town (5) |
| replay | Hednesford Town (5) | 1–0 | Northwich Victoria (5) |
| 8 | Morecambe (5) | 1–0 | Bishop Auckland (6) |
| 9 | Marine (6) | 1–1 | Runcorn (6) |
| replay | Runcorn (6) | 3–2 | Marine (6) |
| 10 | Altrincham (5) | 0–0 | Stalybridge Celtic (6) |
| replay | Stalybridge Celtic (6) | X | Altrincham (5) |
| 2-1 result was declared null and void due to a rule break, and the FA ordered a second replay ||||
| 2nd replay | Stalybridge Celtic (6) | 3–2 | Altrincham (5) |
| 11 | Lancaster City (6) | 0–0 | Bamber Bridge (6) |
| replay | Bamber Bridge (6) | 4–3 | Lancaster City (6) |
| 12 | Worthing (7) | 1–1 | Dover Athletic (5) |
| replay | Dover Athletic (5) | 0–1 | Worthing (7) |
| 13 | Oxford City (7) | 2–1 | Salisbury City (6) |
| 14 | Hendon (6) | 1–0 | Margate (6) |
| 15 | Bognor Regis Town (7) | 0–1 | Whyteleafe (7) |
| 16 | Welling United (5) | 2–0 | Kidderminster Harriers (5) |
| Tie | Home team (tier) | Score | Away team (tier) |
| 17 | Merthyr Tydfil (6) | 2–0 | Hitchin Town (6) |
| 18 | Dulwich Hamlet (6) | 0–0 | Hayes (5) |
| replay | Hayes (5) | 3–0 | Dulwich Hamlet (6) |
| 19 | Kingstonian (5) | 0–0 | Boston United (6) |
| replay | Boston United (6) | 0–3 | Kingstonian (5) |
| 20 | Rushden & Diamonds (5) | 4–1 | Sutton United (5) |
| 21 | Ilkeston Town (6) | 3–0 | Romford (7) |
| 22 | Worcester City (6) | 2–5 | Forest Green Rovers (5) |
| 23 | Yeovil Town (5) | 2–1 | Witney Town (7) |
| 24 | Woking (5) | 1–1 | Burton Albion (6) |
| replay | Burton Albion (6) | 3–1 | Woking (5) |
| 25 | Enfield (6) | 1–1 | Baldock Town (7) |
| replay | Baldock Town (7) | 2–2 (2–4 p) | Enfield (6) |
| 26 | Lymington & New Milton | 1–3 | Aldershot Town (6) |
| 27 | Rothwell Town (6) | 1–1 | Kettering Town (5) |
| replay | Kettering Town (5) | 2–1 | Rothwell Town (6) |
| 28 | Canvey Island (6) | 3–3 | St Albans City (6) |
| replay | St Albans City (6) | 2–1 | Canvey Island (6) |
| 29 | Stevenage Borough (5) | 1–1 | Bath City (6) |
| replay | Bath City (6) | 1–0 | Stevenage Borough (5) |
| 30 | Horsham YMCA | 2–3 | Chelmsford City (7) |
| 31 | Hereford United (5) | 4–1 | Burgess Hill Town |
| 32 | Slough Town (6) | 1–1 | Cambridge City (6) |
| replay | Cambridge City (6) | 3–2 | Slough Town (6) |

## 1999–2000 FA Cup

See 1999–2000 FA Cup for details of the rounds from the first round Proper onwards.