| 25/03/2000 | 15:00 | Aston Villa | - | Derby County | 2:0 (1:0) | |
| 15:00 | Bradford City | - | Manchester United | 0:4 (0:2) | ||
| 15:00 | Chelsea FC | - | Southampton FC | 1:1 (0:0) | ||
| 15:00 | Liverpool FC | - | Newcastle United | 2:1 (0:0) | ||
| 15:00 | Middlesbrough FC | - | Sheffield Wednesday | 1:0 (1:0) | ||
| 15:00 | Sunderland AFC | - | Everton FC | 2:1 (1:1) | ||
| 15:00 | Watford FC | - | Tottenham Hotspur | 1:1 (0:0) | ||
| 26/03/2000 | 15:00 | Leicester City | - | Leeds United | 2:1 (1:1) | |
| 16:00 | West Ham United | - | Wimbledon FC | 2:1 (1:0) | ||
| 16:00 | Arsenal FC | - | Coventry City | 3:0 (0:0) |
| » Tables | Home | Away | First round | Second round | First half | Second half |
| # | Team | M. | W | D | L | goals | Dif. | Pt. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
Manchester United | 30 | 20 | 7 | 3 | 69:35 | 34 | 67 |
| 2 |
|
Leeds United | 30 | 19 | 3 | 8 | 49:33 | 16 | 60 |
| 3 |
|
Liverpool FC | 30 | 16 | 7 | 7 | 44:26 | 18 | 55 |
| 4 |
|
Arsenal FC | 30 | 16 | 6 | 8 | 53:31 | 22 | 54 |
| 5 |
|
Chelsea FC | 30 | 14 | 10 | 6 | 40:26 | 14 | 52 |
| 6 |
|
Aston Villa | 30 | 12 | 9 | 9 | 35:27 | 8 | 45 |
| 7 |
|
Sunderland AFC | 30 | 12 | 9 | 9 | 48:45 | 3 | 45 |
| 8 |
|
West Ham United | 30 | 12 | 9 | 9 | 41:40 | 1 | 45 |
| 9 |
|
Leicester City | 30 | 13 | 5 | 12 | 45:43 | 2 | 44 |
| 10 |
|
Tottenham Hotspur | 30 | 12 | 7 | 11 | 45:35 | 10 | 43 |
| 11 |
|
Everton FC | 30 | 10 | 11 | 9 | 49:41 | 8 | 41 |
| 12 |
|
Newcastle United | 30 | 11 | 7 | 12 | 50:44 | 6 | 40 |
| 13 |
|
Middlesbrough FC | 30 | 11 | 7 | 12 | 32:40 | -8 | 40 |
| 14 |
|
Coventry City | 30 | 9 | 8 | 13 | 39:39 | 0 | 35 |
| 15 |
|
Southampton FC | 30 | 9 | 7 | 14 | 36:52 | -16 | 34 |
| 16 |
|
Wimbledon FC | 30 | 7 | 11 | 12 | 41:56 | -15 | 32 |
| 17 |
|
Derby County | 30 | 7 | 7 | 16 | 33:46 | -13 | 28 |
| 18 |
|
Bradford City | 30 | 6 | 8 | 16 | 28:53 | -25 | 26 |
| 19 |
|
Sheffield Wednesday | 30 | 5 | 6 | 19 | 27:57 | -30 | 21 |
| 20 |
|
Watford FC | 30 | 5 | 4 | 21 | 26:61 | -35 | 19 |