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Details of Chelsea's 1998-99 FA Cup campaign.
| Date | Rnd | Team | At | Score | Att | Scorers |
| Sat, 02 Jan 99 | 3rd | Oldham Athletic | (a) | 2-0 | 12,770 | Vialli 2 |
| Mon, 25 Jan 99 | 4th | Oxford United | (a) | 1-1 | 9,059 | Leboeuf |
| Wed, 03 Feb 99 | 4th | Oxford United | (h) | 4-2 | 32,106 | Wise, Forrsell 2, Zola |
| Sat, 13 Feb 99 | 5th | Sheffield Wednesday | (a) | 1-0 | 29,410 | Di Matteo |
| Sun, 07 Mar 99 | 6th | Manchester United | (a) | 0-0 | 54,587 | |
| Wed, 10 Mar 99 | 6th | Manchester United | (h) | 0-2 | 33,075 |