1998–99 FA Cup Third round Third round

| Tie_no | Home_team | Score | Away_team | Attendance |
|---|---|---|---|---|
| 21 | Coventry City | 7–0 | Macclesfield Town | 2 January 1999 |
| 22 | West Ham United | 1–1 | Swansea City | 2 January 1999 |
| Replay | Swansea City | 1–0 | West Ham United | 13 January 1999 |
| 23 | Manchester United | 3–1 | Middlesbrough | 3 January 1999 |
| 24 | Plymouth Argyle | 0–3 | Derby County | 2 January 1999 |
| 25 | Bradford City | 2–1 | Grimsby Town | 2 January 1999 |
| 26 | Oldham Athletic | 0–2 | Chelsea | 2 January 1999 |
| 27 | Wimbledon | 1–0 | Manchester City | 2 January 1999 |
| 28 | Cardiff City | 1–1 | Yeovil Town | 2 January 1999 |
| Replay | Yeovil Town | 1–2 | Cardiff City | 12 January 1999 |
| 29 | Port Vale | 0–3 | Liverpool | 16557 |
| 30 | Southport | 0–2 | Leyton Orient | 2 January 1999 |