| Club: | Tottenham Hotspur |
| Season: | 1898–99 |
| Manager: | Frank Brettell |
| Stadium: | Northumberland Park |
| League: | Southern League |
| League Result: | 7th |
| League2: | United League |
| League2 Result: | 4th |
| League3: | Thames & Medway League |
| League3 Result: | 4th |
| Cup1: | FA Cup |
| Cup1 Result: | 3rd round |
| League Topscorer: | John Cameron (11) |
| Prevseason: | 1897–98 |
| Nextseason: | 1899–1900 |
The 1898–99 season was Tottenham's third season as a fully professional club and the 16th year in existence. They competed in three leagues this season along with a long run in the FA Cup. In the Southern League Tottenham finished in 7th place. This was the clubs final appearance in the United League where they finished in fourth place. This was also the only season that Tottenham played in the Thames & Medway League.
In the FA Cup Tottenham played Luton Town three times finally managing to beat them 2–0 at Tufnell Park. Making it through the first round with two games played against Newton Heath (Who later became Manchester United). The second round saw a home tie against Sunderland which Tottenham over come to progress to the third round to face Stoke only to loose 4–1.
| Date from | Position | Nationality | Name | From | Fee | Ref. | |
|---|---|---|---|---|---|---|---|
| May 1898 | Forward | John Cameron | Unknown | ||||
| May 1898 | Forward | Tommy Atherton | Unknown | ||||
| May 1898 | Forward | Robert Cain | Unknown |
| Date from | Position | Nationality | Name | To | Fee | Ref. | |
|---|---|---|---|---|---|---|---|
| December 1898 | Forward | James Davidson | Brighton United | Released | |||
| 1898 | Full back | Joe Knowles | Sunderland | Released |
See main article: 1898–99 Southern Football League.
See main article: United League (football).
| Pos | Club | P | W | D | L | F | A | Pts | |
|---|---|---|---|---|---|---|---|---|---|
| 1 | Millwall Athletic | 20 | 14 | 3 | 3 | 42 | 19 | 31 | |
| 2 | Southampton | 20 | 12 | 1 | 7 | 52 | 32 | 25 | |
| 3 | Woolwich Arsenal | 20 | 10 | 4 | 6 | 30 | 30 | 24 | |
| 4 | Tottenham Hotspur | 20 | 11 | 2 | 7 | 36 | 25 | 24 | |
| 5 | Bristol City | 20 | 11 | 0 | 9 | 43 | 31 | 22 | |
| 6 | Reading | 20 | 8 | 5 | 7 | 36 | 25 | 21 | |
| 7 | Brighton United | 20 | 10 | 1 | 9 | 41 | 42 | 21 | |
| 8 | Wellingborough | 20 | 7 | 1 | 12 | 32 | 40 | 15 | |
| 9 | Kettering Town | 20 | 8 | 1 | 11 | 25 | 38 | 15 | |
| 10 | Rushden | 20 | 6 | 1 | 13 | 26 | 45 | 13 | |
| 11 | Luton Town | 20 | 2 | 3 | 15 | 24 | 71 | 7 |
1898–99 season was the only season that Tottenham played in this league. The table is recorded in Phil Sour's Tottenham Hotspur The Official Illustrated History 1882–1995.
| Pos | Club | P | W | D | L | F | A | Pts | |
|---|---|---|---|---|---|---|---|---|---|
| 1 | New Brompton | 16 | 13 | 1 | 2 | 47 | 15 | 27 | |
| 2 | Gravesend United | 16 | 12 | 1 | 3 | 53 | 21 | 25 | |
| 3 | Chatham | 16 | 10 | 3 | 3 | 41 | 11 | 23 | |
| 4 | Tottenham Hotspur | 16 | 11 | 0 | 5 | 34 | 28 | 22 | |
| 5 | Thames Ironworks | 16 | 7 | 2 | 7 | 23 | 24 | 16 | |
| 6 | Sheppey United | 16 | 7 | 1 | 8 | 31 | 31 | 15 | |
| 7 | RETB | 16 | 2 | 2 | 12 | 24 | 49 | 6 | |
| 8 | Grays United | 16 | 2 | 2 | 12 | 11 | 42 | 6 | |
| 9 | Dartford | 16 | 2 | 0 | 14 | 21 | 64 | 4 |
See main article: 1898–99 FA Cup.