1955–56 FA Cup Second Round Proper Second Round Proper

| Tie_no | Home_team | Score | Away_team | Date_ |
|---|---|---|---|---|
| 1 | Chesterfield | 1–2 | Hartlepools United | 10 December 1955 |
| 2 | Darlington | 0–1 | Accrington Stanley | 10 December 1955 |
| 3 | Weymouth | 0–1 | Southend United | 10 December 1955 |
| 4 | Reading | 2–2 | Aldershot | 10 December 1955 |
| Replay | Aldershot | 3–0 | Reading | 14 December 1955 |
| 5 | Walsall | 2–1 | Southampton | 10 December 1955 |
| 6 | Derby County | 1–6 | Boston United | 10 December 1955 |
| 7 | Swindon Town | 1–1 | Peterborough United | 10 December 1955 |
| Replay | Peterborough United | 1–2 | Swindon Town | 15 December 1955 |
| 8 | Shrewsbury Town | 0–0 | Torquay United | 10 December 1955 |
| Replay | Torquay United | 5–1 | Shrewsbury Town | 14 December 1955 |