1998–99 FA Cup Fifth round Fifth round

| Tie_no | Home_team | Score | Away_team | Attendance |
|---|---|---|---|---|
| 1 | Sheffield Wednesday | 0–1 | Chelsea | 13 February 1999 |
| 2 | Everton | 2–1 | Coventry City | 13 February 1999 |
| 3 | Newcastle United | 0–0 | Blackburn Rovers | 14 February 1999 |
| Replay | Blackburn Rovers | 0–1 | Newcastle United | 24 February 1999 |
| 4 | Barnsley | 4–1 | Bristol Rovers | 13 February 1999 |
| 5 | Manchester United | 1–0 | Fulham | 14 February 1999 |
| 6 | Huddersfield Town | 2–2 | Derby County | 13 February 1999 |
| Replay | Derby County | 3–1 | Huddersfield Town | 24 February 1999 |
| 7 | Arsenal | 2–1 | Sheffield United | 13 February 1999 |
| Replay | Arsenal | 2–1 | Sheffield United | 23 February 1999 |
| 8 | Leeds United | 1–1 | Tottenham Hotspur | 13 February 1999 |
| Replay | Tottenham Hotspur | 2–0 | Leeds United | 24 February 1999 |