 |
 |
|
|
| 30/10/1999 | 14:00 | Derby County | - | Chelsea FC | 3:1 (1:1) | |
| 14:00 | Leeds United | - | West Ham United | 1:0 (0:0) | ||
| 14:00 | Leicester City | - | Sheffield Wednesday | 3:0 (2:0) | ||
| 14:00 | Arsenal FC | - | Newcastle United | 0:0 (0:0) | ||
| 14:00 | Manchester United | - | Aston Villa | 3:0 (2:0) | ||
| 14:00 | Middlesbrough FC | - | Everton FC | 2:1 (1:1) | ||
| 14:00 | Wimbledon FC | - | Southampton FC | 1:1 (0:0) | ||
| 31/10/1999 | 14:00 | Sunderland AFC | - | Tottenham Hotspur | 2:1 (2:0) | |
| 15:00 | Coventry City | - | Watford FC | 4:0 (2:0) | ||
| 01/11/1999 | 19:00 | Liverpool FC | - | Bradford City | 3:1 (2:1) |
| » Tables | Home | Away | First round | Second round | First half | Second half |
| # | Team | M. | W | D | L | goals | Dif. | Pt. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
Leeds United | 13 | 9 | 2 | 2 | 26:16 | 10 | 29 |
| 2 |
|
Manchester United | 13 | 8 | 3 | 2 | 31:19 | 12 | 27 |
| 3 |
|
Sunderland AFC | 13 | 8 | 3 | 2 | 23:11 | 12 | 27 |
| 4 |
|
Arsenal FC | 13 | 8 | 2 | 3 | 20:12 | 8 | 26 |
| 5 |
|
Chelsea FC | 13 | 7 | 2 | 4 | 20:11 | 9 | 23 |
| 6 |
|
Leicester City | 13 | 7 | 2 | 4 | 23:17 | 6 | 23 |
| 7 |
|
Liverpool FC | 13 | 6 | 3 | 4 | 16:12 | 4 | 21 |
| 8 |
|
Middlesbrough FC | 13 | 7 | 0 | 6 | 18:17 | 1 | 21 |
| 9 |
|
Tottenham Hotspur | 13 | 6 | 2 | 5 | 21:18 | 3 | 20 |
| 10 |
|
West Ham United | 13 | 6 | 2 | 5 | 14:11 | 3 | 20 |
| 11 |
|
Everton FC | 13 | 5 | 3 | 5 | 22:20 | 2 | 18 |
| 12 |
|
Aston Villa | 13 | 5 | 3 | 5 | 13:15 | -2 | 18 |
| 13 |
|
Coventry City | 13 | 4 | 4 | 5 | 20:15 | 5 | 16 |
| 14 |
|
Southampton FC | 13 | 3 | 4 | 6 | 19:25 | -6 | 13 |
| 15 |
|
Wimbledon FC | 13 | 2 | 7 | 4 | 19:27 | -8 | 13 |
| 16 |
|
Derby County | 13 | 3 | 3 | 7 | 13:22 | -9 | 12 |
| 17 |
|
Bradford City | 13 | 3 | 3 | 7 | 11:21 | -10 | 12 |
| 18 |
|
Newcastle United | 13 | 3 | 2 | 8 | 23:27 | -4 | 11 |
| 19 |
|
Watford FC | 13 | 3 | 0 | 10 | 8:22 | -14 | 9 |
| 20 |
|
Sheffield Wednesday | 13 | 1 | 2 | 10 | 8:30 | -22 | 5 |
