 |
 |
|
|
| 02/10/1999 | 14:00 | Aston Villa | - | Liverpool FC | 0:0 (0:0) | |
| 14:00 | Bradford City | - | Sunderland AFC | 0:4 (0:1) | ||
| 14:00 | Everton FC | - | Coventry City | 1:1 (1:1) | ||
| 14:00 | Sheffield Wednesday | - | Wimbledon FC | 5:1 (2:1) | ||
| 03/10/1999 | 13:00 | Tottenham Hotspur | - | Leicester City | 2:3 (2:1) | |
| 13:00 | Watford FC | - | Leeds United | 1:2 (1:1) | ||
| 13:00 | West Ham United | - | Arsenal FC | 2:1 (1:0) | ||
| 14:00 | Newcastle United | - | Middlesbrough FC | 2:1 (2:0) | ||
| 15:00 | Chelsea FC | - | Manchester United | 5:0 (2:0) | ||
| 04/10/1999 | 19:00 | Southampton FC | - | Derby County | 3:3 (2:1) |
| » Tables | Home | Away | First round | Second round | First half | Second half |
| # | Team | M. | W | D | L | goals | Dif. | Pt. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
Chelsea FC | 10 | 7 | 2 | 1 | 17:4 | 13 | 23 |
| 2 |
|
Leeds United | 10 | 7 | 1 | 2 | 19:12 | 7 | 22 |
| 3 |
|
Manchester United | 10 | 6 | 3 | 1 | 23:15 | 8 | 21 |
| 4 |
|
Sunderland AFC | 10 | 6 | 2 | 2 | 18:8 | 10 | 20 |
| 5 |
|
West Ham United | 10 | 6 | 1 | 3 | 13:7 | 6 | 19 |
| 6 |
|
Arsenal FC | 10 | 6 | 1 | 3 | 13:9 | 4 | 19 |
| 7 |
|
Everton FC | 10 | 5 | 2 | 3 | 16:10 | 6 | 17 |
| 8 |
|
Leicester City | 10 | 5 | 2 | 3 | 17:13 | 4 | 17 |
| 9 |
|
Aston Villa | 10 | 5 | 2 | 3 | 11:9 | 2 | 17 |
| 10 |
|
Tottenham Hotspur | 10 | 4 | 2 | 4 | 16:15 | 1 | 14 |
| 11 |
|
Liverpool FC | 10 | 4 | 2 | 4 | 11:10 | 1 | 14 |
| 12 |
|
Middlesbrough FC | 10 | 4 | 0 | 6 | 11:15 | -4 | 12 |
| 13 |
|
Southampton FC | 10 | 3 | 2 | 5 | 16:21 | -5 | 11 |
| 14 |
|
Coventry City | 10 | 2 | 3 | 5 | 12:14 | -2 | 9 |
| 15 |
|
Watford FC | 10 | 3 | 0 | 7 | 6:11 | -5 | 9 |
| 16 |
|
Derby County | 10 | 2 | 3 | 5 | 10:18 | -8 | 9 |
| 17 |
|
Bradford City | 10 | 2 | 3 | 5 | 5:14 | -9 | 9 |
| 18 |
|
Wimbledon FC | 10 | 1 | 5 | 4 | 14:23 | -9 | 8 |
| 19 |
|
Newcastle United | 10 | 2 | 1 | 7 | 20:23 | -3 | 7 |
| 20 |
|
Sheffield Wednesday | 10 | 1 | 1 | 8 | 8:25 | -17 | 4 |
