# 1989–90 Football League Cup

The 1989–90 Football League Cup (known as the Littlewoods Challenge Cup for sponsorship reasons) was the 30th season of the Football League Cup, a knockout competition for England's top 92 football clubs.
The competition began on 21 August 1989, and ended with the final on 29 April 1990 at the Old Wembley Stadium. The cup was won by Nottingham Forest who beat Oldham Athletic in the final, who regained the trophy after winning it the previous season. This was the second time that Nottingham Forest had won the trophy in successive seasons, having won previously in 1978 and 1979.

## First round

A total of 56 teams took part in the first round. All of the Third Division and Fourth Division sides entered, with eight of the Second Division clubs also starting in this round. The eight clubs consisted of the three teams promoted from the Third Division and the five teams finishing 17th to 21st in the Second Division from the 1988–89 season. Each tie was played across two legs.

### First leg

| Home Team | Score | Away Team | Date |
| Birmingham City | 2–1 | Chesterfield | 22 August 1989 |
| Blackpool | 2–2 | Burnley | 22 August 1989 |
| Brighton and Hove Albion | 0–3 | Brentford | 23 August 1989 |
| Bristol City | 2–3 | Reading | 22 August 1989 |
| Bristol Rovers | 1–0 | Portsmouth | 23 August 1989 |
| Cambridge United | 3–1 | Maidstone United (1897) | 22 August 1989 |
| Cardiff City | 0–3 | Plymouth Argyle | 22 August 1989 |
| Colchester United | 3–4 | Southend United | 22 August 1989 |
| Crewe Alexandra | 4–0 | Chester City | 22 August 1989 |
| Exeter City | 3–0 | Swansea City | 23 August 1989 |
| Fulham | 0–1 | Oxford United | 23 August 1989 |
| Gillingham | 1–4 | Leyton Orient | 22 August 1989 |
| Halifax Town | 3–1 | Carlisle United | 22 August 1989 |
| Hartlepool United | 3–3 | York City | 23 August 1989 |
| Huddersfield Town | 1–1 | Doncaster Rovers | 22 August 1989 |
| Hull City | 1–0 | Grimsby Town | 22 August 1989 |
| Mansfield Town | 1–1 | Northampton Town | 22 August 1989 |
| Peterborough United | 2–0 | Aldershot | 23 August 1989 |
| Preston North End | 3–4 | Tranmere Rovers | 22 August 1989 |
| Rochdale | 2–1 | Bolton Wanderers | 22 August 1989 |
| Scarborough | 2–0 | Scunthorpe United | 22 August 1989 |
| Sheffield United | 1–1 | Rotherham United | 22 August 1989 |
| Shrewsbury Town | 3–0 | Notts County | 22 August 1989 |
| Stockport County | 1–0 | Bury | 21 August 1989 |
| Torquay United | 1–0 | Hereford United | 22 August 1989 |
| Walsall | 1–2 | Port Vale | 22 August 1989 |
| Wolverhampton Wanderers | 1–0 | Lincoln City | 22 August 1989 |
| Wrexham | 0–0 | Wigan Athletic | 22 August 1989 |

### Second leg

| Home Team | Score | Away Team | Date | Agg |
| Aldershot | 6–2 | Peterborough United | 29 August 1989 | 6–4 |
| Bolton Wanderers | 5–1 | Rochdale | 29 August 1989 | 6–3 |
| Brentford | 1–1 | Brighton and Hove Albion | 29 August 1989 | 4–1 |
| Burnley | 0–1 | Blackpool | 29 August 1989 | 2–3 |
| Bury | 1–1 | Stockport County | 29 August 1989 | 1–2 |
| Carlisle United | 1–0 | Halifax Town | 29 August 1989 | 2–3 |
| Chester City | 0–2 | Crewe Alexandra | 29 August 1989 | 0–6 |
| Chesterfield | 1–1 | Birmingham City | 29 August 1989 | 2–3 |
| Doncaster Rovers | 1–2 | Huddersfield Town | 29 August 1989 | 2–3 |
| Grimsby Town | 2–0 | Hull City | 29 August 1989 | 2–1 |
| Hereford United | 3–0 | Torquay United | 30 August 1989 | 3–1 |
| Leyton Orient | 3–0 | Gillingham | 29 August 1989 | 7–1 |
| Lincoln City | 0–2 | Wolverhampton Wanderers | 30 August 1989 | 0–3 |
| Maidstone United (1897) | 0–1 | Cambridge United | 30 August 1989 | 1–4 |
| Northampton Town | 0–2 | Mansfield Town | 5 September 1989 | 1–3 |
| Notts County | 3–1 | Shrewsbury Town | 29 August 1989 | 3–4 |
| Oxford United | 3–5 | Fulham | 30 August 1989 | 4–5 |
| Plymouth Argyle | 0–2 | Cardiff City | 29 August 1989 | 3–2 |
| Port Vale | 1–0 | Walsall | 28 August 1989 | 3–1 |
| Portsmouth | 2–0 | Bristol Rovers | 29 August 1989 | 2–1 |
| Reading | 2–2 | Bristol City | 29 August 1989 | 5–4 |
| Rotherham United | 1–0 | Sheffield United | 29 August 1989 | 2–1 |
| Scunthorpe United | 1–1 | Scarborough | 29 August 1989 | 1–3 |
| Southend United | 2–1 | Colchester United | 29 August 1989 | 6–4 |
| Swansea City | 1–1 | Exeter City | 29 August 1989 | 1–4 |
| Tranmere Rovers | 3–1 | Preston North End | 29 August 1989 | 7–4 |
| Wigan Athletic | 5–0 | Wrexham | 30 August 1989 | 5–0 |
| York City | 4–1 | Hartlepool United | 29 August 1989 | 7–4 |

## Second round

A total of 64 teams took part in the second round, including the 28 winners from round one. The remaining Second Division clubs entered in this round, as well as the 20 sides from the First Division. Each tie was again played across two legs.

### First leg

| Home Team | Score | Away Team | Date |
| Arsenal | 2–0 | Plymouth Argyle | 19 September 1989 |
| Aston Villa | 2–1 | Wolverhampton Wanderers | 20 September 1989 |
| Barnsley | 1–1 | Blackpool | 19 September 1989 |
| Birmingham City | 1–2 | West Ham United | 19 September 1989 |
| Bolton Wanderers | 2–1 | Watford | 19 September 1989 |
| Brentford | 2–1 | Manchester City | 19 September 1989 |
| Cambridge United | 2–1 | Derby County | 19 September 1989 |
| Charlton Athletic | 3–1 | Hereford United | 20 September 1989 |
| Chelsea | 1–1 | Scarborough | 19 September 1989 |
| Crewe Alexandra | 0–1 | Bournemouth | 19 September 1989 |
| Crystal Palace | 1–2 | Leicester City | 19 September 1989 |
| Exeter City | 3–0 | Blackburn Rovers | 20 September 1989 |
| Grimsby Town | 3–1 | Coventry City | 19 September 1989 |
| Ipswich Town | 0–1 | Tranmere Rovers | 19 September 1989 |
| Leyton Orient | 0–2 | Everton | 19 September 1989 |
| Liverpool | 5–2 | Wigan Athletic | 19 September 1989 |
| Mansfield Town | 3–4 | Luton Town | 19 September 1989 |
| Middlesbrough | 4–0 | Halifax Town | 20 September 1989 |
| Norwich City | 1–1 | Rotherham United | 20 September 1989 |
| Nottingham Forest | 1–1 | Huddersfield Town | 20 September 1989 |
| Oldham Athletic | 2–1 | Leeds United | 19 September 1989 |
| Port Vale | 1–2 | Wimbledon | 18 September 1989 |
| Portsmouth | 2–3 | Manchester United | 20 September 1989 |
| Queens Park Rangers | 2–1 | Stockport County | 20 September 1989 |
| Reading | 3–1 | Newcastle United | 19 September 1989 |
| Sheffield Wednesday | 0–0 | Aldershot | 20 September 1989 |
| Shrewsbury Town | 0–3 | Swindon Town | 19 September 1989 |
| Stoke City | 1–0 | Millwall | 19 September 1989 |
| Sunderland | 1–1 | Fulham | 19 September 1989 |
| Tottenham Hotspur | 1–0 | Southend United | 20 September 1989 |
| West Bromwich Albion | 1–3 | Bradford City | 20 September 1989 |
| York City | 0–1 | Southampton | 20 September 1989 |

### Second leg

| Home Team | Score | Away Team | Date | Agg |
| Aldershot | 0–8 | Sheffield Wednesday | 3 October 1989 | 0–8 |
| Blackburn Rovers | 2–1 | Exeter City | 3 October 1989 | 2–4 |
| Blackpool | 1–1 | Barnsley | 3 October 1989 | 2–2 |
| Bournemouth | 0–0 | Crewe Alexandra | 3 October 1989 | 1–0 |
| Bradford City | 3–5 | West Bromwich Albion | 4 October 1989 | 6–6 |
| Coventry City | 3–0 | Grimsby Town | 4 October 1989 | 4–3 |
| Derby County | 5–0 | Cambridge United | 4 October 1989 | 6–2 |
| Everton | 2–2 | Leyton Orient | 3 October 1989 | 4–2 |
| Fulham | 0–3 | Sunderland | 3 October 1989 | 1–4 |
| Halifax Town | 0–1 | Middlesbrough | 3 October 1989 | 0–5 |
| Hereford United | 0–1 | Charlton Athletic | 4 October 1989 | 1–4 |
| Huddersfield Town | 3–3 | Nottingham Forest | 3 October 1989 | 4–4 |
| Leeds United | 1–2 | Oldham Athletic | 3 October 1989 | 2–4 |
| Leicester City | 2–3 | Crystal Palace | 4 October 1989 | 4–4 |
| Luton Town | 7–2 | Mansfield Town | 3 October 1989 | 11–5 |
| Manchester City | 4–1 | Brentford | 4 October 1989 | 5–3 |
| Manchester United | 0–0 | Portsmouth | 3 October 1989 | 3–2 |
| Millwall | 2–0 | Stoke City | 4 October 1989 | 2–1 |
| Newcastle United | 4–0 | Reading | 4 October 1989 | 5–3 |
| Plymouth Argyle | 1–6 | Arsenal | 3 October 1989 | 1–8 |
| Rotherham United | 0–2 | Norwich City | 3 October 1989 | 1–3 |
| Scarborough | 3–2 | Chelsea | 4 October 1989 | 4–3 |
| Southampton | 2–0 | York City | 3 October 1989 | 3–0 |
| Southend United | 3–2 | Tottenham Hotspur | 4 October 1989 | 3–3 |
| Stockport County | 0–0 | Queens Park Rangers | 2 October 1989 | 1–2 |
| Swindon Town | 3–1 | Shrewsbury Town | 3 October 1989 | 6–1 |
| Tranmere Rovers | 1–0 | Ipswich Town | 3 October 1989 | 2–0 |
| Watford | 1–1 | Bolton Wanderers | 3 October 1989 | 2–3 |
| West Ham United | 1–1 | Birmingham City | 4 October 1989 | 3–2 |
| Wigan Athletic | 0–3 | Liverpool | 4 October 1989 | 2–8 |
| Wimbledon | 3–0 | Port Vale | 4 October 1989 | 5–1 |
| Wolverhampton Wanderers | 1–1 | Aston Villa | 4 October 1989 | 2–3 |

## Third round

A total of 32 teams took part in the third round, all 32 winners from round two. Unlike the previous two rounds, this round was played over one leg. Frank Bunn scores a new League Cup record six goals in Oldham's 7–0 victory over Scarborough.

### Ties

| Home team | Result | Away team | Date |
| Arsenal | 1–0 | Liverpool | 25 October 1989 |
| Aston Villa | 0–0 | West Ham United | 25 October 1989 |
| Crystal Palace | 0–0 | Nottingham Forest | 24 October 1989 |
| Derby County | 2–1 | Sheffield Wednesday | 25 October 1989 |
| Everton | 3–0 | Luton Town | 24 October 1989 |
| Exeter City | 3–0 | Blackpool | 25 October 1989 |
| Manchester City | 3–1 | Norwich City | 25 October 1989 |
| Manchester United | 0–3 | Tottenham Hotspur | 25 October 1989 |
| Middlesbrough | 1–1 | Wimbledon | 25 October 1989 |
| Newcastle United | 0–1 | West Bromwich Albion | 25 October 1989 |
| Oldham Athletic | 7–0 | Scarborough | 25 October 1989 |
| Queens Park Rangers | 1–2 | Coventry City | 25 October 1989 |
| Southampton | 1–0 | Charlton Athletic | 24 October 1989 |
| Sunderland | 1–1 | Bournemouth | 24 October 1989 |
| Swindon Town | 3–3 | Bolton Wanderers | 24 October 1989 |
| Tranmere Rovers | 3–2 | Millwall | 23 October 1989 |

### Replays

| Home team | Result | Away team | Date |
| Bolton Wanderers | 1–1 | Swindon Town | 7 November 1989 |
| Bournemouth | 0–1 | Sunderland | 7 November 1989 |
| Nottingham Forest | 5–0 | Crystal Palace | 1 November 1989 |
| West Ham United | 1–0 | Aston Villa | 8 November 1989 |
| Wimbledon | 1–0 | Middlesbrough | 8 November 1989 |

### 2nd Replay

| Home team | Result | Away team | Date |
| Bolton Wanderers | 1–1 | Swindon Town | 14 November 1989 |

### 3rd Replay

| Home team | Result | Away team | Date |
| Swindon Town | 2–1 | Bolton Wanderers | 20 November 1989 |

## Fourth round

A total of 16 teams took part in the fourth round, all 16 winners from round three. Once again this round was played over one leg.

### Ties

| Home team | Result | Away team | Date |
| Derby County | 2–0 | West Bromwich Albion | 22 November 1989 |
| Exeter City | 2–2 | Sunderland | 29 November 1989 |
| Manchester City | 0–1 | Coventry City | 22 November 1989 |
| Nottingham Forest | 1–0 | Everton | 22 November 1989 |
| Oldham Athletic | 3–1 | Arsenal | 22 November 1989 |
| Swindon Town | 0–0 | Southampton | 29 November 1989 |
| Tranmere Rovers | 2–2 | Tottenham Hotspur | 22 November 1989 |
| West Ham United | 1–0 | Wimbledon | 22 November 1989 |

### Replays

| Home team | Result | Away team | Date |
| Southampton | 4–2 | Swindon Town | 16 January 1990 |
| Sunderland | 5–2 | Exeter City | 5 December 1989 |
| Tottenham Hotspur | 4–0 | Tranmere Rovers | 29 November 1989 |

## Fifth round

The eight winners from the fourth round took part in the fifth round. Once again this round was played over one leg.

### 2nd Replay
## Semi-finals

As with the first two rounds, the semi-final ties were played over two legs. Holders Nottingham Forest narrowly defeated Coventry City, while West Ham United bowed out in the semi-finals for the second year running, this time at the hands of Oldham Athletic 6–3 on aggregate. Oldham's 6-0 first leg victory all but sealed their first ever appearance in a major final and at Wembley, was a record for a league cup semi-final until Manchester City defeated Burton Albion 9–0 in the first-leg of the semi-final tie in 2019. Five years earlier, in 2014, City had equaled Oldham's record, again at the expense of West Ham, with a 6-0 first-leg semi-final victory, and on that occasion City's 3–0 win in the second leg at Upton Park had set a record for an aggregate victory (9-0) which City themselves surpassed in 2019 with a 1-0 second-leg win at Burton for a 10-0 aggregate semi-final win.

### Second leg

Nottingham Forest won 2–1 on aggregate.
Oldham Athletic won 6–3 on aggregate.