| Tottenham Hotspur | Season 1998-1999 | Played | Won | Drew | Lost | For | Against | Points | ||||||||
| Premiership - 11th | 38 | 11 | 14 | 13 | 46 | 50 | 47 | |||||||||
| F.A. Cup | 7 | 4 | 2 | 1 | 13 | 6 | SemiFinal | |||||||||
| Managers Gross/Pleat/Graham | League Cup - Winners | 8 | 7 | 1 | 0 | 17 | 7 | Winners | ||||||||
| Games attended 29 | Total 1998/99 | 53 | 22 | 17 | 14 | 76 | 63 | 11th | ||||||||
| 15-Aug-98 | FA Prem | 23,031 | A | * | Wimbledon | L | 1 | - | 3 | Fox | ||||||
| 22-Aug-98 | FA Prem | 32,129 | H | * | Sheffield Wednesday | L | 0 | - | 3 | |||||||
| 29-Aug-98 | FA Prem | 39,379 | A | Everton | W | 1 | - | 0 | Ferdinand | |||||||
| 09-Sep-98 | FA Prem | 28,331 | H | * | Blackburn Rovers | W | 2 | - | 1 | Ferdinand, Nielsen | ||||||
| 13-Sep-98 | FA Prem | 30,345 | H | * | Middlesbrough | L | 0 | - | 3 | |||||||
| 19-Sep-98 | FA Prem | 15,204 | A | Southampton | D | 1 | - | 1 | Fox | |||||||
| 26-Sep-98 | FA Prem | 35,535 | H | * | Leeds United | D | 3 | - | 3 | Vega, Iversen, Campbell | ||||||
| 03-Oct-98 | FA Prem | 30,093 | A | * | Derby County | W | 1 | - | 0 | Campbell | ||||||
| 19-Oct-98 | FA Prem | 20,787 | A | Leicester City | L | 1 | - | 2 | Ferdinand | |||||||
| 24-Oct-98 | FA Prem | 36,047 | H | * | Newcastle United | W | 2 | - | 0 | Iversen (2) | ||||||
| 02-Nov-98 | FA Prem | 32,202 | H | * | Charlton Athletic | D | 2 | - | 2 | Nielsen, Armstrong | ||||||
| 07-Nov-98 | FA Prem | 39,241 | A | * | Aston Villa | L | 2 | - | 3 | Anderton (pen), Vega | ||||||
| 14-Nov-98 | FA Prem | 38,278 | A | Arsenal | D | 0 | - | 0 | ||||||||
| 21-Nov-98 | FA Prem | 35,832 | H | Nottingham Forest | W | 2 | - | 0 | Armstrong, Nielsen | |||||||
| 28-Nov-98 | FA Prem | 26,044 | A | * | West Ham United | L | 1 | - | 2 | Armstrong | ||||||
| 05-Dec-98 | FA Prem | 36,125 | H | * | Liverpool | W | 2 | - | 1 | Fox, Carragher o.g. | ||||||
| 12-Dec-98 | FA Prem | 36,097 | H | * | Manchester United | D | 2 | - | 2 | Campbell (2) | ||||||
| 19-Dec-98 | FA Prem | 34,881 | A | Chelsea | L | 0 | - | 2 | ||||||||
| 26-Dec-98 | FA Prem | 23,098 | A | Coventry City | D | 1 | - | 1 | Campbell | |||||||
| 28-Dec-98 | FA Prem | 36,053 | H | Everton | W | 4 | - | 1 | Ferdinand, Armstrong | |||||||
| 09-Jan-99 | FA Prem | 28,204 | A | Sheffield Wednesday | D | 0 | - | 0 | ||||||||
| 16-Jan-99 | FA Prem | 32,422 | H | * | Wimbledon | D | 0 | - | 0 | |||||||
| 30-Jan-99 | FA Prem | 29,396 | A | Blackburn Rovers | D | 1 | - | 1 | Iversen | |||||||
| 06-Feb-99 | FA Prem | 34,376 | H | * | Coventry City | D | 0 | - | 0 | |||||||
| 20-Feb-99 | FA Prem | 34,687 | A | Middlesbrough | D | 0 | - | 0 | ||||||||
| 27-Feb-99 | FA Prem | 35,392 | H | * | Derby County | D | 1 | - | 1 | Sherwood | ||||||
| 02-Mar-99 | FA Prem | 28,580 | H | * | Southampton | W | 3 | - | 0 | Armstrong, Iversen, Dominguez | ||||||
| 10-Mar-99 | FA Prem | 34,521 | A | Leeds United | L | 0 | - | 2 | ||||||||
| 13-Mar-99 | FA Prem | 35,963 | H | * | Aston Villa | W | 1 | - | 0 | Sherwood | ||||||
| 03-Apr-99 | FA Prem | 34,415 | H | * | Leicester City | L | 0 | - | 2 | |||||||
| 05-Apr-99 | FA Prem | 36,655 | A | Newcastle United | D | 1 | - | 1 | Anderton (pen), | |||||||
| 17-Apr-99 | FA Prem | 25,181 | A | Nottingham Forest | W | 1 | - | 0 | Iversen | |||||||
| 20-Apr-99 | FA Prem | 20,043 | A | Charlton Athletic | W | 4 | - | 1 | Iversen, Campbell, Dominguez, Ginola | |||||||
| 24-Apr-99 | FA Prem | 36,089 | H | * | West Ham United | L | 0 | - | 2 | Ginola | ||||||
| 01-May-99 | FA Prem | 44,007 | A | * | Liverpool | L | 2 | - | 3 | Carragher o.g., Iversen | ||||||
| 05-May-99 | FA Prem | 36,019 | H | * | Arsenal | L | 1 | - | 3 | Anderton | ||||||
| 10-May-99 | FA Prem | 35,878 | H | * | Chelsea | D | 2 | - | 2 | Iversen, Ginola | ||||||
| 16-May-99 | FA Prem | 55,189 | A | Manchester United | L | 1 | - | 2 | Ferdinand | |||||||
| Tottenham Hotspur in the FA Cup - Season 1998-1999 | ||||||||||||||||
| 02-Jan-99 | F.A. Cup 3 | 36,022 | H | * | Watford | W | 5 | - | 2 | Iversen (2), Anderton (pen), Nielsen, Fox | ||||||
| 23-Jan-99 | F.A. Cup 4 | 22,229 | A | * | Wimbledon | D | 1 | - | 1 | Ginola | ||||||
| 02-Feb-99 | F.A. Cup 4® | 24,049 | H | * | Wimbledon | W | 3 | - | 0 | Sinton, Nielsen (2) | ||||||
| 13-Feb-99 | F.A. Cup 5 | 39,696 | A | Leeds United | D | 1 | - | 1 | Sherwood | |||||||
| 24-Feb-99 | F.A. Cup 5® | 32,307 | H | Leeds United | W | 2 | - | 0 | Anderton, Ginola | |||||||
| 16-Mar-99 | F.A. Cup 6 | 18,793 | A | Barnsley | W | 1 | - | 0 | Ginola | |||||||
| 11-Apr-99 | F.A. Cup SF | 53,609 | OT | Newcastle United | L | 0 | - | 2 | (a.e.t) | |||||||
| Tottenham Hotspur in the league Cup - Season 1998-1999 WINNERS | ||||||||||||||||
| 15-Sep-98 | L.C. Cup 2 (1L) | 11,831 | A | Brentford | W | 3 | - | 2 | Carr, Dominguez, Vega | |||||||
| 23-Sep-98 | L.C. Cup 2 (2L) | 22,980 | H | * | Brentford | W | 3 | - | 2 | Nielsen, Campbell, Armstrong | ||||||
| 27-Oct-98 | L.C. Cup 3 | 7,422 | A | Northampton Town | W | 3 | - | 1 | Armstrong (2), Campbell | |||||||
| 10-Nov-98 | L.C. Cup 4 | 20,772 | A | Liverpool | W | 3 | - | 1 | Iversen, Scales, Nielsen | |||||||
| 02-Dec-98 | L.C. Cup 5 | 35,702 | H | * | Manchester United | W | 3 | - | 1 | Armstrong (2), Ginola | ||||||
| 27-Jan-99 | L.C. Cup SF (1L) | 35,997 | H | * | Wimbledon | D | 0 | - | 0 | |||||||
| 16-Feb-99 | L.C. Cup SF (2L) | 25,204 | A | Wimbledon | W | 1 | - | 0 | Iversen | |||||||
| 21-Mar-99 | L.C. Cup FINAL | 77,892 | W | * | Leicester City | W | 1 | - | 0 | Nielsen | ||||||