34. Round | 22/04/2000 | Chelsea FC | - | Middlesbrough FC | 1:1 | ||||
35. Round | 24/04/2000 | Manchester United | - | Chelsea FC | 3:2 | ||||
36. Round | 29/04/2000 | Chelsea FC | - | Liverpool FC | 2:0 | ||||
37. Round | 06/05/2000 | Arsenal FC | - | Chelsea FC | 2:1 | ||||
38. Round | 14/05/2000 | Chelsea FC | - | Derby County | 4:0 |