| 1999/05/22 | Manchester United |  | 2-0 |  | Newcastle |
| 1999/04/14 | Arsenal |  | 1-2 d.t.s. | | Manchester United |
| 1999/03/10 | Chelsea |  | 0-2 | | Manchester United |
| 1999/02/02 | Tottenham |  | 3-0 |  | Wimbledon | ||||
| 1999/02/03 | Huddersfield Town |  | 2-1 |  | Wrexham | ||||
| Chelsea | | 4-2 |  | Oxford United |
| 1999/01/12 | Yeovil Town |  | 1-2 d.t.s. |  | Cardiff City | ||||
| 1999/01/13 | Swansea City |  | 1-0 |  | West Ham | ||||
| Leeds United |  | 3-1 |  | Rushden & Diamonds | |||||
| Fulham |  | 1-0 |  | Southampton | |||||
| 1999/01/19 | Barnsley |  | 3-1 |  | Swindon Town | ||||
| 1999/01/23 | Notts County |  | 3-4 d.t.s. |  | Sheffield United |
| 1 |
|
Alan Shearer Newcastle | 5 G |
| 3 |
|
Karl Connolly Wrexham | 4 G |
| 4 |
|
Kevin Nugent Cardiff City | 3 G |
| 4 |
|
Gary Jones Notts County | 3 G |
