 |
 |
|
|
| 18/09/1999 | 14:00 | Aston Villa | - | Bradford City | 1:0 (0:0) | |
| 14:00 | Derby County | - | Sunderland AFC | 0:5 (0:2) | ||
| 14:00 | Leicester City | - | Liverpool FC | 2:2 (1:2) | ||
| 14:00 | Manchester United | - | Wimbledon FC | 1:1 (0:1) | ||
| 14:00 | Southampton FC | - | Arsenal FC | 0:1 (0:0) | ||
| 14:00 | Watford FC | - | Chelsea FC | 1:0 (0:0) | ||
| 19/09/1999 | 13:00 | Tottenham Hotspur | - | Coventry City | 3:2 (1:0) | |
| 14:00 | Newcastle United | - | Sheffield Wednesday | 8:0 (4:0) | ||
| 15:00 | Everton FC | - | West Ham United | 1:0 (0:0) | ||
| 15:00 | Leeds United | - | Middlesbrough FC | 2:0 (1:0) |
| » Tables | Home | Away | First round | Second round | First half | Second half |
| # | Team | M. | W | D | L | goals | Dif. | Pt. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
Manchester United | 8 | 6 | 2 | 0 | 20:7 | 13 | 20 |
| 2 |
|
Chelsea FC | 8 | 5 | 2 | 1 | 11:4 | 7 | 17 |
| 3 |
|
West Ham United | 8 | 5 | 1 | 2 | 11:5 | 6 | 16 |
| 4 |
|
Leeds United | 8 | 5 | 1 | 2 | 14:9 | 5 | 16 |
| 5 |
|
Arsenal FC | 8 | 5 | 1 | 2 | 11:7 | 4 | 16 |
| 6 |
|
Aston Villa | 8 | 5 | 1 | 2 | 10:6 | 4 | 16 |
| 7 |
|
Sunderland AFC | 8 | 4 | 2 | 2 | 13:8 | 5 | 14 |
| 8 |
|
Everton FC | 8 | 4 | 1 | 3 | 14:9 | 5 | 13 |
| 9 |
|
Tottenham Hotspur | 8 | 4 | 1 | 3 | 13:11 | 2 | 13 |
| 10 |
|
Liverpool FC | 8 | 4 | 1 | 3 | 11:9 | 2 | 13 |
| 11 |
|
Middlesbrough FC | 8 | 4 | 0 | 4 | 10:12 | -2 | 12 |
| 12 |
|
Leicester City | 8 | 3 | 2 | 3 | 11:10 | 1 | 11 |
| 13 |
|
Watford FC | 8 | 3 | 0 | 5 | 5:8 | -3 | 9 |
| 14 |
|
Southampton FC | 8 | 3 | 0 | 5 | 10:15 | -5 | 9 |
| 15 |
|
Derby County | 8 | 2 | 2 | 4 | 7:14 | -7 | 8 |
| 16 |
|
Wimbledon FC | 8 | 1 | 4 | 3 | 12:17 | -5 | 7 |
| 17 |
|
Bradford City | 8 | 1 | 3 | 4 | 4:10 | -6 | 6 |
| 18 |
|
Coventry City | 8 | 1 | 2 | 5 | 10:13 | -3 | 5 |
| 19 |
|
Newcastle United | 8 | 1 | 1 | 6 | 16:19 | -3 | 4 |
| 20 |
|
Sheffield Wednesday | 8 | 0 | 1 | 7 | 3:23 | -20 | 1 |
