# 1899 Wimbledon Championships – Men's singles

Arthur Gore defeated Sydney Smith 3–6, 6–1, 6–2, 6–4 in the All Comers' Final, but the reigning champion Reginald Doherty defeated Gore 1–6, 4–6, 6–3, 6–3, 6–3 in the challenge round to win the gentlemen's singles tennis title at the 1899 Wimbledon Championships.

## Draw
### Key

* Q = Qualifier
* WC = Wild card
* LL = Lucky loser
* Alt = Alternate
* SE = Special exempt
* PR = Protected ranking
* ITF = ITF entry
* JE = Junior exempt
* w/o = Walkover
* r = Retired
* d = Defaulted
* SR = Special ranking

### Challenge round

| Challenge Round | Challenge Round | Challenge Round | Challenge Round | Challenge Round | Challenge Round | Challenge Round |
| Arthur Gore | Arthur Gore | 6 | 6 | 3 | 3 | 3 |
| Reginald Doherty | Reginald Doherty | 1 | 4 | 6 | 6 | 6 |

### All comers' finals

| Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals | Semifinals | Semifinals | Semifinals | Semifinals | Final | Final | Final | Final | Final | Final |
| Philip Pearson | Philip Pearson | 3 | 2 | 7 | | | | | | | | | | | | | | |
| Arthur Gore | Arthur Gore | 6 | 6 | 9 | | | | | | | | | | | | | | |
| Arthur Gore | Arthur Gore | 6 | 6 | 9 | | Arthur Gore | Arthur Gore | 6 | 4 | 3 | 7 | 6 | | | | | | |
| | | | | | | Harold Mahony | Harold Mahony | 3 | 6 | 6 | 5 | 1 | | | | | | |
| George Greville | George Greville | 3 | 7 | 6 | 8 | Harold Mahony | Harold Mahony | 3 | 6 | 6 | 5 | 1 | | | | | | |
| Harold Mahony | Harold Mahony | 6 | 9 | 2 | 10 | | | | | | | | | | | | | |
| Harold Mahony | Harold Mahony | 6 | 9 | 2 | 10 | | | | | | | | Arthur Gore | Arthur Gore | 3 | 6 | 6 | 6 |
| | | | | | | | | | | | | | Sydney Smith | Sydney Smith | 6 | 1 | 2 | 4 |
| Harold Nisbet | Harold Nisbet | 3 | 5 | 4 | | | | | | | | | | | | | | | Sydney Smith | Sydney Smith | 6 | 1 | 2 | 4 |
| Sydney Smith | Sydney Smith | 6 | 7 | 6 | | | | | | | | | | | | | | |
| Sydney Smith | Sydney Smith | 6 | 7 | 6 | | Sydney Smith | Sydney Smith | 2 | 11 | 4 | 8 | 8 | | | | | | |
| | | | | | | Herbert Roper Barrett | Herbert Roper Barrett | 6 | 9 | 6 | 6 | 6 | | | | | | |
| Clarence Hobart | Clarence Hobart | 6 | 5 | 4 | | Herbert Roper Barrett | Herbert Roper Barrett | 6 | 9 | 6 | 6 | 6 | | | | | | |
| Herbert Roper Barrett | Herbert Roper Barrett | 8 | 7 | 6 | | | | | | | | | | | | | | |

### Top half
#### Section 1

| Second round | Second round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Third round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| Philip Pearson | Philip Pearson | 6 | 6 | 6 | | | | | | | | | | | | |
| Frederick Plaskitt | Frederick Plaskitt | 1 | 0 | 3 | | | | | | | | | | | | |
| | | | | | | | P Pearson | P Pearson | 6 | 6 | 6 | | | | | |
| | | | | | | | M Ritchie | M Ritchie | 3 | 2 | 4 | | | | | |
| Major Ritchie | Major Ritchie | 6 | 3 | 6 | 4 | 6 | | | | | | | | | | |
| Wilberforce Eaves | Wilberforce Eaves | 4 | 6 | 4 | 6 | 4 | | | | | | | | | | |
| | | | | | | | | | | | | P Pearson | P Pearson | 3 | 2 | 7 |
| | | | | | | | | | | | | A Gore | A Gore | 6 | 6 | 9 |
| Arthur Gore | Arthur Gore | 8 | 6 | 6 | | | | | | | | | | | | |
| Ambrose Dudley | Ambrose Dudley | 6 | 2 | 3 | | | | | | | | | | | | |
| | | | | | | | A Gore | A Gore | 6 | 6 | 6 | | | | | |
| | | | | | | | G Caridia | G Caridia | 2 | 1 | 4 | | | | | |
| SVR Drapes | SVR Drapes | 2 | 4 | 1 | | | | | | | | | | | | |
| George Caridia | George Caridia | 6 | 6 | 6 | | | | | | | | | | | | |

#### Section 2

| First round | First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Third round | Third round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| | | | | | | George Hillyard | George Hillyard | w/o | | | | | | | | | | | | | | | |
| | | | | | | George Greville | George Greville | | | | | | | | | | | | | | | | |
| | | | | | | | | | | | | G Greville | G Greville | 6 | 6 | 6 | | | | | | | |
| | | | | | | | | | | | | MRL White | MRL White | 0 | 3 | 2 | | | | | | | |
| | | | | | | MRL White | MRL White | 5 | 7 | 6 | 6 | | | | | | | | | | | | |
| | | | | | | Archibald McNair | Archibald McNair | 7 | 5 | 4 | 1 | | | | | | | | | | | | |
| | | | | | | | | | | | | | | | | | | G Greville | G Greville | 3 | 7 | 6 | 8 |
| | | | | | | | | | | | | | | | | | | H Mahony | H Mahony | 6 | 9 | 2 | 10 |
| | | | | | | Alexander Mackay | Alexander Mackay | 1 | 0 | 1 | | | | | | | | | | | | | |
| George Simond | George Simond | | | | | G Simond | G Simond | 6 | 6 | 6 | | | | | | | | | | | | | |
| Clement Cazalet | Clement Cazalet | w/o | | | | | | | | | | G Simond | G Simond | 2 | 6 | 6 | 2 | | | | | | |
| Harold Mahony | Harold Mahony | | | | | | | | | | | H Mahony | H Mahony | 6 | 4 | 8 | 6 | | | | | | |
| William Doherty | William Doherty | w/o | | | | H Mahony | H Mahony | 6 | 7 | 6 | | | | | | | | | | | | | |
| David Hawes | David Hawes | 7 | 6 | 5 | 6 | D Hawes | D Hawes | 3 | 5 | 2 | | | | | | | | | | | | | |
| Frederick Payn | Frederick Payn | 5 | 0 | 7 | 3 | | | | | | | | | | | | | | | | | | |

### Bottom half
#### Section 3

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Third round | Third round | Third round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| Harold Nisbet | Harold Nisbet | 6 | 6 | 6 | | | | | | | | | | | | | | | | | | | |
| J Johnstone | J Johnstone | 0 | 3 | 1 | H Nisbet | H Nisbet | 6 | 6 | 6 | | | | | | | | | | | | | | |
| Roy Allen | Roy Allen | 6 | 7 | 7 | R Allen | R Allen | 3 | 4 | 0 | | | | | | | | | | | | | | |
| Nelson Wright | Nelson Wright | 4 | 5 | 5 | | | | | | | | H Nisbet | H Nisbet | 6 | 6 | 6 | | | | | | | |
| | | | | | | | | | | | | M Day | M Day | 4 | 3 | 3 | | | | | | | |
| | | | | | Maurice Day | Maurice Day | 1 | 2 | 6 | 6 | 6 | | | | | | | | | | | | |
| | | | | | Allan Pearson | Allan Pearson | 6 | 6 | 3 | 4 | 1 | | | | | | | | | | | | |
| | | | | | | | | | | | | | | | | | | | H Nisbet | H Nisbet | 3 | 5 | 4 |
| | | | | | | | | | | | | | | | | | | | S Smith | S Smith | 6 | 7 | 6 |
| | | | | | John Flavelle | John Flavelle | | | | | | | | | | | | | | | | | |
| | | | | | Roderick McNair | Roderick McNair | w/o | | | | | | | | | | | | | | | | |
| | | | | | | | | | | | | J Flavelle | J Flavelle | 6 | 6 | 1 | 5 | 2 | | | | | |
| | | | | | | | | | | | | S Smith | S Smith | 4 | 4 | 6 | 7 | 6 | | | | | |
| | | | | | Sydney Smith | Sydney Smith | 6 | 6 | 6 | | | | | | | | | | | | | | |
| | | | | | E Reynolds | E Reynolds | 1 | 1 | 1 | | | | | | | | | | | | | | |

#### Section 4

| Second round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Third round | Third round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| James Crispe | James Crispe | 6 | 6 | 6 | | | | | | | | | | | | |
| B Wood-Hill | B Wood-Hill | 3 | 3 | 1 | | | | | | | | | | | | |
| | | | | | | J Crispe | J Crispe | 3 | 6 | 7 | 3 | | | | | |
| | | | | | | C Hobart | C Hobart | 6 | 2 | 9 | 6 | | | | | |
| Clarence Hobart | Clarence Hobart | 6 | 6 | 4 | 6 | | | | | | | | | | | |
| Charles Dixon | Charles Dixon | 3 | 1 | 6 | 2 | | | | | | | | | | | |
| | | | | | | | | | | | | C Hobart | C Hobart | 6 | 5 | 4 |
| | | | | | | | | | | | | HR Barrett | HR Barrett | 8 | 7 | 6 |
| Oswald Milne | Oswald Milne | 4 | 10 | 3 | 8 | | | | | | | | | | | |
| Robert Hough | Robert Hough | 6 | 8 | 6 | 10 | | | | | | | | | | | |
| | | | | | | R Hough | R Hough | 1 | 3 | 3 | | | | | | |
| | | | | | | HR Barrett | HR Barrett | 6 | 6 | 6 | | | | | | |
| Charles Allen | Charles Allen | 0 | 0 | 0 | | | | | | | | | | | | |
| Herbert Roper Barrett | Herbert Roper Barrett | 6 | 6 | 6 | | | | | | | | | | | | |