1998–99 FA Cup First round First round

| Tie_no | Home_team | Score | Away_team | Attendance |
|---|---|---|---|---|
| 1 | Enfield | 2–2 | York City | 14 November 1998 |
| Replay | York City | 2–1 | Enfield | 24 November 1998 |
| 2 | Darlington | 3–2 | Burnley | 17 November 1998 |
| 3 | Bedlington Terriers | 4–1 | Colchester United | 14 November 1998 |
| 4 | Preston North End | 3–0 | Ford United | 14 November 1998 |
| 5 | Yeovil Town | 2–2 | West Auckland Town | 14 November 1998 |
| Replay | West Auckland Town | 1–1 | Yeovil Town | 24 November 1998 |
| Yeovil Town won 5–3 on penalties | Yeovil Town won 5–3 on penalties | Yeovil Town won 5–3 on penalties | Yeovil Town won 5–3 on penalties | Yeovil Town won 5–3 on penalties |
| 6 | Reading | 0–1 | Stoke City | 14 November 1998 |