1988–89 FA Cup First round proper First round proper

| Tie_no | Home_team | Score | Away_team | Date_ |
|---|---|---|---|---|
| 9 | Reading | 4–2 | Hendon | 19 November 1988 |
| 10 | Woking | 1–4 | Cambridge United | 19 November 1988 |
| 11 | Gillingham | 3–3 | Peterborough United | 19 November 1988 |
| Replay | Peterborough United | 1–0 | Gillingham | 23 November 1988 |
| 12 | Bolton Wanderers | 0–0 | Chesterfield | 19 November 1988 |
| Replay | Chesterfield | 2–3 | Bolton Wanderers | 28 November 1988 |
| 13 | Grimsby Town | 1–0 | Wolverhampton Wanderers | 19 November 1988 |
| 14 | Stafford Rangers | 2–2 | Crewe Alexandra | 19 November 1988 |
| Replay | Crewe Alexandra | 3–2 | Stafford Rangers | 22 November 1988 |
| 15 | Scarborough | 2–1 | Stockport County | 19 November 1988 |
| 16 | Doncaster Rovers | 0–0 | Brandon United | 19 November 1988 |
| Replay | Doncaster Rovers | 2–1 | Brandon United | 22 November 1988 |