1998–99 FA Cup Second round Second round

| Tie_no | Home_team | Score | Away_team | Attendance |
|---|---|---|---|---|
| 1 | Darlington | 1–1 | Manchester City | 4 December 1998 |
| Replay | Manchester City | 1–0 | Darlington | 15 December 1998 |
| 2 | Preston North End | 2–0 | Walsall | 5 December 1998 |
| 3 | Rochdale | 0–0 | Rotherham United | 5 December 1998 |
| Replay | Rotherham United | 4–0 | Rochdale | 15 December 1998 |
| 4 | Yeovil Town | 2–0 | Northampton Town | 5 December 1998 |
| 5 | Notts County | 1–1 | Wigan Athletic | 5 December 1998 |
| Replay | Wigan Athletic | 0–0 | Notts County | 15 December 1998 |
| Notts County won 4–2 on penalties | Notts County won 4–2 on penalties | Notts County won 4–2 on penalties | Notts County won 4–2 on penalties | Notts County won 4–2 on penalties |