1998–99 FA Cup First round First round

| Tie_no | Home_team | Score | Away_team | Attendance |
|---|---|---|---|---|
| 14 | Wycombe Wanderers | 1–0 | Chesterfield | 14 November 1998 |
| 15 | Manchester City | 3–0 | Halifax Town | 13 November 1998 |
| 16 | Fulham | 1–1 | Leigh RMI | 15 November 1998 |
| Replay | Leigh RMI | 0–2 | Fulham | 24 November 1998 |
| 17 | Brentford | 5–0 | Camberley Town | 14 November 1998 |
| 18 | Bristol Rovers | 3–0 | Welling United | 14 November 1998 |
| 19 | Northampton Town | 2–1 | Lancaster City | 14 November 1998 |
| 20 | Plymouth Argyle | 0–0 | Kidderminster Harriers | 14 November 1998 |
| Replay | Kidderminster Harriers | 0–0 | Plymouth Argyle | 1 December 1998 |
| Plymouth Argyle won 5–4 on penalties | Plymouth Argyle won 5–4 on penalties | Plymouth Argyle won 5–4 on penalties | Plymouth Argyle won 5–4 on penalties | Plymouth Argyle won 5–4 on penalties |