| Tottenham Hotspur | Season 1999-2000 | Played | Won | Drew | Lost | For | Against | Points | ||||||||
| Premiership - 10th | 38 | 15 | 8 | 15 | 57 | 49 | 53 | |||||||||
| F.A. Cup | 2 | 0 | 1 | 1 | 2 | 7 | 3rd Rnd | |||||||||
| League Cup | 2 | 1 | 0 | 1 | 4 | 4 | 4th Rnd | |||||||||
| Manager: George Graham | UEFA Cup | 4 | 2 | 1 | 1 | 4 | 2 | 2nd Rnd | ||||||||
| Games attended 28 | Total - Season 1999-2000 | 46 | 18 | 10 | 18 | 67 | 62 | 10th | ||||||||
| 07-Aug-99 | FA Prem | 26,010 | A | West Ham United | L | 0 | - | 1 | ||||||||
| 09-Aug-99 | FA Prem | 28,701 | H | * | Newcastle United | W | 3 | - | 1 | Iversen, Ferdinand, Sherwood | ||||||
| 14-Aug-99 | FA Prem | 34,539 | H | * | Everton | W | 3 | - | 2 | Sherwood, Iversen, Leonhardsen | ||||||
| 21-Aug-99 | FA Prem | 24,027 | A | * | Sheffield Wednesday | W | 2 | - | 1 | Ferdinand, Leonhardsen | ||||||
| 28-Aug-99 | FA Prem | 36,012 | H | Leeds United | L | 1 | - | 2 | Sherwood | |||||||
| 12-Sep-99 | FA Prem | 18,143 | A | Bradford City | D | 1 | - | 1 | Perry | |||||||
| 19-Sep-99 | FA Prem | 35,224 | H | * | Coventry City | W | 3 | - | 2 | Iversen, Armstrong, Leonhardsen | ||||||
| 26-Sep-99 | FA Prem | 17,368 | A | Wimbledon | D | 1 | - | 1 | Carr | |||||||
| 03-Oct-99 | FA Prem | 35,591 | H | * | Leicester City | L | 2 | - | 3 | Iversen (2) | ||||||
| 16-Oct-99 | FA Prem | 29,815 | A | * | Derby County | W | 1 | - | 0 | Armstrong | ||||||
| 23-Oct-99 | FA Prem | 36,072 | H | * | Manchester United | W | 3 | - | 1 | Iversen, Scholes o.g., Carr | ||||||
| 31-Oct-99 | FA Prem | 41,904 | A | Sunderland | L | 1 | - | 2 | Iversen | |||||||
| 07-Nov-99 | FA Prem | 36,085 | H | * | Arsenal | W | 2 | - | 1 | Iversen, Sherwood | ||||||
| 20-Nov-99 | FA Prem | 15,248 | A | Southampton | W | 1 | - | 0 | Leonhardsen | |||||||
| 28-Nov-99 | FA Prem | 36,460 | A | Newcastle United | L | 1 | - | 2 | Armstrong | |||||||
| 06-Dec-99 | FA Prem | 36,233 | H | * | West Ham United | D | 0 | - | 0 | |||||||
| 18-Dec-99 | FA Prem | 33,129 | A | Middlesbrough | L | 1 | - | 2 | Vega | |||||||
| 26-Dec-99 | FA Prem | 36,089 | H | * | Watford | W | 4 | - | 0 | Ginola, Iversen, Sherwood (2) | ||||||
| 29-Dec-99 | FA Prem | 39,217 | A | Aston Villa | D | 1 | - | 1 | Sherwood | |||||||
| 03-Jan-00 | FA Prem | 36,044 | H | * | Liverpool | W | 1 | - | 0 | Armstrong | ||||||
| 12-Jan-00 | FA Prem | 34,989 | A | Chelsea | L | 0 | - | 1 | ||||||||
| 15-Jan-00 | FA Prem | 36,144 | A | * | Everton | D | 2 | - | 2 | Armstrong, Ginola | ||||||
| 22-Jan-00 | FA Prem | 35,897 | H | * | Sheffield Wednesday | L | 0 | - | 1 | |||||||
| 05-Feb-00 | FA Prem | 36,041 | H | * | Chelsea | L | 0 | - | 1 | |||||||
| 12-Feb-00 | FA Prem | 40,127 | A | * | Leeds United | L | 0 | - | 1 | |||||||
| 26-Feb-00 | FA Prem | 23,077 | A | * | Coventry City | W | 1 | - | 0 | Armstrong | ||||||
| 04-Mar-00 | FA Prem | 35,472 | H | * | Bradford City | D | 1 | - | 1 | Iversen | ||||||
| 11-Mar-00 | FA Prem | 36,024 | H | * | Southampton | W | 7 | - | 2 | Campbell, Anderton, Armstrong (2), Iversen (3) | ||||||
| 19-Mar-00 | FA Prem | 38,131 | A | * | Arsenal | L | 1 | - | 2 | Armstrong | ||||||
| 25-Mar-00 | FA Prem | 20,050 | A | Watford | D | 1 | - | 1 | Armstrong | |||||||
| 04-Apr-00 | FA Prem | 31,796 | H | * | Middlesbrough | L | 2 | - | 3 | Armstrong, Ginola | ||||||
| 09-Apr-00 | FA Prem | 44,536 | A | Liverpool | L | 0 | - | 2 | ||||||||
| 15-Apr-00 | FA Prem | 35,304 | H | * | Aston Villa | L | 2 | - | 4 | Iversen, Armstrong | ||||||
| 19-Apr-00 | FA Prem | 19,764 | A | Leicester City | W | 1 | - | 0 | Ginola | |||||||
| 22-Apr-00 | FA Prem | 33,086 | H | * | Wimbledon | W | 2 | - | 0 | Armstrong, Anderton | ||||||
| 29-Apr-00 | FA Prem | 33,044 | H | * | Derby County | D | 1 | - | 1 | Clemence | ||||||
| 06-May-00 | FA Prem | 61,629 | A | Manchester United | L | 1 | - | 3 | Armstrong | |||||||
| 14-May-00 | FA Prem | 36,070 | H | * | Sunderland | W | 3 | - | 1 | Anderton (pen), Sherwood, Carr | ||||||
| Tottenham Hotspur in the FA Cup - Season 1999-2000 | ||||||||||||||||
| 12-Dec-99 | F.A. Cup 3 | 33,116 | H | * | Newcastle United | D | 1 | - | 1 | Iversen | ||||||
| 23-Dec-99 | F.A. Cup 3® | 35,415 | A | Newcastle United | L | 1 | - | 6 | Ginola | |||||||
| Tottenham Hotspur in the league Cup - Season 1999-2000 | ||||||||||||||||
| 13-Oct-99 | L.C. Cup 3 | 25,486 | H | * | Crewe Alexandra | W | 3 | - | 1 | Leonhardsen, Ginola, Sherwood, | ||||||
| 01-Dec-99 | L.C. Cup 4 | 18,134 | A | Fulham | L | 1 | - | 3 | Iversen | |||||||
| Tottenham Hotspur in the UEFA Cup - Season 1999-2000 | ||||||||||||||||
| 19-Sep-99 | UEFA. 1 (1L) | 32,660 | H | * | FC Zimbru | W | 3 | - | 0 | Leonhardsen, Perry, Sherwood | ||||||
| 30-Sep-99 | UEFA. 1 (2L) | 7,000 | A | FC Zimbru | D | 0 | - | 0 | ||||||||
| 28-Oct-99 | UEFA. 2 (1L) | 35,177 | H | * | 1FC Kaiserslautern | W | 1 | - | 0 | Iversen (pen) | ||||||
| 04-Nov-99 | UEFA. 2 (2L) | 29,044 | A | 1FC Kaiserslautern | L | 0 | - | 2 | ||||||||