2008–09 FA Cup Fifth Round Proper Fifth Round Proper

| Tie_no | Home_team | Score | Away_team | Attendance |
|---|---|---|---|---|
| 1 | Sheffield United | 1 – 1 | Hull City | 22283 |
| replay | Hull City | 2 – 1 | Sheffield United | 17239 |
| 2 | Watford | 1 – 3 | Chelsea | 16851 |
| 3 | West Ham United | 1 – 1 | Middlesbrough | 33658 |
| replay | Middlesbrough | 2 – 0 | West Ham United | 15602 |
| 4 | Blackburn Rovers | 2 – 2 | Coventry City | 15053 |
| replay | Coventry City | 1 – 0 | Blackburn Rovers | 22793 |
| 5 | Derby County | 1 – 4 | Manchester United | 32103 |
| 6 | Swansea City | 1 – 1 | Fulham | 16573 |
| replay | Fulham | 2 – 1 | Swansea City | 12316 |
| 7 | Everton | 3 – 1 | Aston Villa | 35439 |
| 8 | Arsenal | 3 – 0 | Burnley | 57454 |