| 17. Round | 04/12/1999 | Sunderland AFC | - | Chelsea FC | 4:1 | ||||
| 26. Round | 26/02/2000 | Sunderland AFC | - | Derby County | 1:1 | ||||
| 28. Round | 11/03/2000 | Liverpool FC | - | Sunderland AFC | 1:1 |  |
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| 29. Round | 18/03/2000 | Sunderland AFC | - | Middlesbrough FC | 1:1 | ||||
| 32. Round | 08/04/2000 | Sunderland AFC | - | Wimbledon FC | 2:1 | ||||
| 36. Round | 29/04/2000 | Aston Villa | - | Sunderland AFC | 1:1 | ||||
| 37. Round | 06/05/2000 | Sunderland AFC | - | West Ham United | 1:0 | |
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| 38. Round | 14/05/2000 | Tottenham Hotspur | - | Sunderland AFC | 3:1 |
England