1998–99 FA Cup First round First round

| Tie_no | Home_team | Score | Away_team | Attendance |
|---|---|---|---|---|
| 7 | Walsall | 1–0 | Gresley Rovers | 14 November 1998 |
| 8 | Woking | 0–1 | Scunthorpe United | 14 November 1998 |
| 9 | Boreham Wood | 2–3 | Luton Town | 15 November 1998 |
| 10 | Macclesfield Town | 2–2 | Slough Town | 14 November 1998 |
| Replay | Slough Town | 1–1 | Macclesfield Town | 24 November 1998 |
| Macclesfield Town won 9–8 on penalties | Macclesfield Town won 9–8 on penalties | Macclesfield Town won 9–8 on penalties | Macclesfield Town won 9–8 on penalties | Macclesfield Town won 9–8 on penalties |
| 11 | Scarborough | 1–1 | Rochdale | 14 November 1998 |
| Replay | Rochdale | 2–0 | Scarborough | 24 November 1998 |
| 12 | Wrexham | 1–0 | Peterborough United | 14 November 1998 |
| 13 | Hednesford Town | 3–1 | Barnet | 14 November 1998 |