| 26/02/2000 | 14:00 | Arsenal FC | - | Southampton FC | 3:1 (2:0) | |
| 14:00 | Bradford City | - | Aston Villa | 1:1 (0:1) | ||
| 14:00 | Chelsea FC | - | Watford FC | 2:1 (1:1) | ||
| 14:00 | Coventry City | - | Tottenham Hotspur | 0:1 (0:0) | ||
| 14:00 | Middlesbrough FC | - | Leeds United | 0:0 (0:0) | ||
| 14:00 | Sheffield Wednesday | - | Newcastle United | 0:2 (0:1) | ||
| 14:00 | Sunderland AFC | - | Derby County | 1:1 (0:0) | ||
| 14:00 | West Ham United | - | Everton FC | 0:4 (0:1) | ||
| 14:00 | Wimbledon FC | - | Manchester United | 2:2 (1:1) | ||
| 03/05/2000 | 18:45 | Liverpool FC | - | Leicester City | 0:2 (0:1) |
| » Tables | Home | Away | First round | Second round | First half | Second half |
| # | Team | M. | W | D | L | goals | Dif. | Pt. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
Manchester United | 26 | 17 | 6 | 3 | 59:33 | 26 | 57 |
| 2 |
|
Leeds United | 26 | 16 | 3 | 7 | 39:29 | 10 | 51 |
| 3 |
|
Arsenal FC | 26 | 14 | 5 | 7 | 46:27 | 19 | 47 |
| 4 |
|
Liverpool FC | 26 | 14 | 5 | 7 | 38:23 | 15 | 47 |
| 5 |
|
Chelsea FC | 26 | 13 | 7 | 6 | 37:24 | 13 | 46 |
| 6 |
|
Sunderland AFC | 26 | 11 | 7 | 8 | 42:37 | 5 | 40 |
| 7 |
|
Everton FC | 26 | 10 | 9 | 7 | 46:35 | 11 | 39 |
| 8 |
|
Aston Villa | 26 | 10 | 8 | 8 | 31:24 | 7 | 38 |
| 9 |
|
Tottenham Hotspur | 26 | 11 | 5 | 10 | 35:29 | 6 | 38 |
| 10 |
|
Leicester City | 26 | 11 | 5 | 10 | 37:36 | 1 | 38 |
| 11 |
|
West Ham United | 26 | 10 | 8 | 8 | 36:35 | 1 | 38 |
| 12 |
|
Newcastle United | 26 | 9 | 7 | 10 | 46:41 | 5 | 34 |
| 13 |
|
Coventry City | 26 | 8 | 8 | 10 | 35:32 | 3 | 32 |
| 14 |
|
Middlesbrough FC | 26 | 9 | 5 | 12 | 27:37 | -10 | 32 |
| 15 |
|
Wimbledon FC | 26 | 6 | 11 | 9 | 37:45 | -8 | 29 |
| 16 |
|
Southampton FC | 26 | 8 | 5 | 13 | 30:43 | -13 | 29 |
| 17 |
|
Derby County | 26 | 6 | 7 | 13 | 28:39 | -11 | 25 |
| 18 |
|
Bradford City | 26 | 6 | 7 | 13 | 26:42 | -16 | 25 |
| 19 |
|
Sheffield Wednesday | 26 | 4 | 5 | 17 | 23:53 | -30 | 17 |
| 20 |
|
Watford FC | 26 | 4 | 3 | 19 | 23:57 | -34 | 15 |