01.08.99 Arsenal (N) Charity Shield     
08.08.99 Everton (A) Premiership     
11.08.99 Sheffield Wednesday (H) Premiership     
14.08.99 Leeds United (H) Premiership     
22.08.99 Arsenal (A) Premiership     
25.08.99 Coventry City (A) Premiership     
27.08.99 Lazio European Super Cup      
28.08.99 Newcastle United (H) Premiership      
 
11.09.99 Liverpool (A) Premiership     
18.09.99 Wimbledon (H) Premiership      
25.09.99 Southampton (H) Premiership      
 
03.10.99 Chelsea (A) Premiership     
16.10.99 Watford (H) Premiership      
23.10.99 Tottenham Hotspur (A) Premiership      
30.10.99 Aston Villa (H) Premiership     
 
06.11.99 Leicester City (A) Premiership      
20.11.99 Derby County (A) Premiership      
27.11.99 Sheffield Wednesday (A) Premiership     
30.11.98 Palmeiras (N) World Club Cup      
 
04.12.99 Everton (H) Premiership     
18.12.99 West Ham (A) Premiership      
26.12.99 Bradford City (H) Premiership     
28.12.99 Sunderland (A) Premiership      
 
03.01.00 Middlesbrough (H) Premiership     
15.01.00 Leeds United (A) Premiership      
22.01.00 Arsenal (H) Premiership      
 
05.02.00 Coventry (H) Premiership     
12.02.00 Newcastle United (A) Premiership      
26.02.00 Wimbledon (A) Premiership     
 
04.03.00 Liverpool (H) Premiership      
11.03.00 Derby County (H) Premiership     
18.03.00 Leicester City (A) Premiership      
25.03.00 Bradford Ciry (A) Premiership      
 
01.04.00 West Ham (H) Premiership      
08.04.00 Middlesbrough (A) Premiership      
15.04.00 Sunderland (H) Premiership      
22.04.00 Southampton (A) Premiership     
24.04.00 Chelsea (H) Premiership      
29.04.00 Watford (A) Premiership      
 
06.05.00 Tottenham Hotspur (H) Premiership     
14.05.00 Aston Villa (A) Premiership