 |
 |
|
|
| 14/08/1999 | 14:00 | Bradford City | - | Sheffield Wednesday | 1:1 (0:1) | |
| 14:00 | Derby County | - | Middlesbrough FC | 1:3 (1:2) | ||
| 14:00 | Leicester City | - | Chelsea FC | 2:2 (1:0) | ||
| 14:00 | Liverpool FC | - | Watford FC | 0:1 (0:1) | ||
| 14:00 | Manchester United | - | Leeds United | 2:0 (0:0) | ||
| 14:00 | Sunderland AFC | - | Arsenal FC | 0:0 (0:0) | ||
| 14:00 | Tottenham Hotspur | - | Everton FC | 3:2 (1:1) | ||
| 14:00 | Wimbledon FC | - | Coventry City | 1:1 (0:0) | ||
| 15/08/1999 | 15:00 | Southampton FC | - | Newcastle United | 4:2 (0:1) | |
| 16/08/1999 | 19:00 | Aston Villa | - | West Ham United | 2:2 (1:1) |
| » Tables | Home | Away | First round | Second round | First half | Second half |
| # | Team | M. | W | D | L | goals | Dif. | Pt. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
Manchester United | 3 | 2 | 1 | 0 | 7:1 | 6 | 7 |
| 2 |
|
Aston Villa | 3 | 2 | 1 | 0 | 6:2 | 4 | 7 |
| 3 |
|
Arsenal FC | 3 | 2 | 1 | 0 | 4:2 | 2 | 7 |
| 4 |
|
Middlesbrough FC | 3 | 2 | 0 | 1 | 6:4 | 2 | 6 |
|
Tottenham Hotspur | 3 | 2 | 0 | 1 | 6:4 | 2 | 6 | |
| 6 |
|
Liverpool FC | 3 | 2 | 0 | 1 | 3:2 | 1 | 6 |
| 7 |
|
Southampton FC | 3 | 2 | 0 | 1 | 5:5 | 0 | 6 |
| 8 |
|
Chelsea FC | 3 | 1 | 2 | 0 | 7:3 | 4 | 5 |
| 9 |
|
Bradford City | 3 | 1 | 2 | 0 | 3:2 | 1 | 5 |
| 10 |
|
Leeds United | 3 | 1 | 1 | 1 | 3:2 | 1 | 4 |
| 11 |
|
Wimbledon FC | 3 | 1 | 1 | 1 | 6:6 | 0 | 4 |
| 12 |
|
Leicester City | 3 | 1 | 1 | 1 | 4:4 | 0 | 4 |
| 13 |
|
West Ham United | 3 | 1 | 1 | 1 | 3:3 | 0 | 4 |
| 14 |
|
Sunderland AFC | 3 | 1 | 1 | 1 | 2:4 | -2 | 4 |
| 15 |
|
Watford FC | 3 | 1 | 0 | 2 | 3:5 | -2 | 3 |
| 16 |
|
Coventry City | 3 | 0 | 1 | 2 | 1:3 | -2 | 1 |
| 17 |
|
Derby County | 3 | 0 | 1 | 2 | 2:5 | -3 | 1 |
| 18 |
|
Everton FC | 3 | 0 | 1 | 2 | 3:7 | -4 | 1 |
| 19 |
|
Sheffield Wednesday | 3 | 0 | 1 | 2 | 2:7 | -5 | 1 |
| 20 |
|
Newcastle United | 3 | 0 | 0 | 3 | 3:8 | -5 | 0 |
