1998–99 FA Cup Second round Second round

| Tie_no | Home_team | Score | Away_team | Attendance |
|---|---|---|---|---|
| Oldham Athletic won 4–2 on penalties | Oldham Athletic won 4–2 on penalties | Oldham Athletic won 4–2 on penalties | Oldham Athletic won 4–2 on penalties | Oldham Athletic won 4–2 on penalties |
| 14 | Exeter City | 2–2 | Bristol Rovers | 5 December 1998 |
| Replay | Bristol Rovers | 5–0 | Exeter City | 15 December 1998 |
| 15 | Scunthorpe United | 2–0 | Bedlington Terriers | 5 December 1998 |
| 16 | Mansfield Town | 1–2 | Southport | 5 December 1998 |
| 17 | Cardiff City | 3–1 | Hednesford Town | 5 December 1998 |
| 18 | Kingstonian | 0–0 | Leyton Orient | 6 December 1998 |
| Replay | Leyton Orient | 2–1 | Kingstonian | 15 December 1998 |
| 19 | Torquay United | 0–1 | Bournemouth | 5 December 1998 |
| 20 | Swansea City | 1–0 | Stoke City | 5 December 1998 |