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Fixture List- 1999/2000 Friendly
| Date | H/A | Opponent | Competition | Score | Attd | Scorers |
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| Sat 10th Jul | H | Chelsea | Friendly | 0-3 | n/a | |
| Tue 13th Jul | H | Southampton | Friendly | 1-2 | n/a | Pitcher |
| Wed 14th Jul | H | West Ham United | Friendly | 1-4 | n/a | Fry |
| Sat 17th Jul | A | Harrow Borough | Friendly | 3-2 | n/a | Akuamoah, Marshall, Pitcher |
| Wed 21st Jul | H | Brentford | Friendly | 2-0 | n/a | Luckett (pen), Marshall |
| Fri 23rd Jul | A | Tiverton Town | Friendly | 4-3 | 415 | Wingfield, Pitcher, Akuamoah (2) |
| Fri 30th Jul | H | Brighton & Hove Albion | Friendly | 1-1 | n/a | Wingfield |
| Tue 3rd Aug | A | Whitstable Town | Friendly | 5-0 | n/a | Akumoah, Crossley, Harris, Leworthy, Smith |
| Sat 7th Aug | A | Newport IoW | Friendly | 1-3 | n/a | Wingfield |
| Tue 26th Oct | H | Reading | Friendly | 1-2 | 118 | Taylor |
| Tue 14th Dec | A | Portfield | Friendly | 8-0 | n/a | Pitcher (2), O'Connor (2), Wingfield (2), Kadi, Leworthy |
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