1990–91 FA Cup Second Round Proper Second Round Proper

| Tie_no | Home_team | Score | Away_team | Date_ |
|---|---|---|---|---|
| 1 | Chesterfield | 3–4 | Bolton Wanderers | 11/12/1990 |
| 2 | Bournemouth | 1–0 | Hayes | 08/12/1990 |
| 3 | Barnet | 0–0 | Northampton Town | 08/12/1990 |
| Replay | Northampton Town | 0–1 | Barnet | 12/12/1990 |
| 4 | Burnley | 2–0 | Stoke City | 12/12/1990 |
| 5 | Woking | 5–1 | Merthyr Tydfil | 08/12/1990 |
| 6 | Crewe Alexandra | 1–0 | Atherstone United | 12/12/1990 |
| 7 | Shrewsbury Town | 1–0 | Chorley | 11/12/1990 |
| 8 | Wycombe Wanderers | 1–1 | Peterborough United | 12/12/1990 |
| Replay | Peterborough United | 2–0 | Wycombe Wanderers | 17/12/1990 |
| 9 | Fulham | 0–0 | Cambridge United | 07/12/1990 |
| Replay | Cambridge United | 2–1 | Fulham | 11/12/1990 |
| 10 | Whitley Bay | 0–1 | Barrow | 12/12/1990 |
| 11 | Scunthorpe United | 3–2 | Tranmere Rovers | 08/12/1990 |
| 12 | Huddersfield Town | 0–2 | Blackpool | 10/12/1990 |
| 13 | Mansfield Town | 2–1 | York City | 17/12/1990 |