FA Cup 02/01/1999 Tottenham Hotspur - Watford FC 5:2 36.022
Pr. League 16/01/1999 Tottenham Hotspur - Wimbledon FC 0:0 32.422
League Cup 27/01/1999 Tottenham Hotspur - Wimbledon FC 0:0 35.997
FA Cup 02/02/1999 Tottenham Hotspur - Wimbledon FC 3:0 24.049
Pr. League 06/02/1999 Tottenham Hotspur - Coventry City 0:0 34.376
FA Cup 24/02/1999 Tottenham Hotspur - Leeds United 2:0 32.307
Pr. League 27/02/1999 Tottenham Hotspur - Derby County 1:1 35.392
Pr. League 02/03/1999 Tottenham Hotspur - Southampton FC 3:0 28.580
Pr. League 13/03/1999 Tottenham Hotspur - Aston Villa 1:0 35.963
Pr. League 03/04/1999 Tottenham Hotspur - Leicester City 0:2 35.415
Pr. League 24/04/1999 Tottenham Hotspur - West Ham United 1:2 36.089
Pr. League 05/05/1999 Tottenham Hotspur - Arsenal FC 1:3 36.019
Pr. League 10/05/1999 Tottenham Hotspur - Chelsea FC 2:2 35.878
Pr. League 09/08/1999 Tottenham Hotspur - Newcastle United 3:1 28.701
Pr. League 14/08/1999 Tottenham Hotspur - Everton FC 3:2 34.539
Pr. League 28/08/1999 Tottenham Hotspur - Leeds United 1:2 36.012
EL 16/09/1999 Tottenham Hotspur - FC Zimbru 3:0 32.660
Pr. League 19/09/1999 Tottenham Hotspur - Coventry City 3:2 35.224
Pr. League 03/10/1999 Tottenham Hotspur - Leicester City 2:3 35.591
League Cup 13/10/1999 Tottenham Hotspur - Crewe Alexandra 3:1 25.486
Pr. League 23/10/1999 Tottenham Hotspur - Manchester United 3:1 36.072
EL 28/10/1999 Tottenham Hotspur - 1. FC Kaiserslautern 1:0 35.177
Pr. League 07/11/1999 Tottenham Hotspur - Arsenal FC 2:1 36.085
Pr. League 06/12/1999 Tottenham Hotspur - West Ham United 0:0 36.233
FA Cup 12/12/1999 Tottenham Hotspur - Newcastle United 1:1 33.116
Pr. League 26/12/1999 Tottenham Hotspur - Watford FC 4:0 36.089