David Brewer defeated Richard Bloomfield 2-6 6-2 6-4 in the Great Britain F1 round of 16 on hard. The upset overturned the form book — Richard Bloomfield came in leading the head-to-head 4–0. David Brewer claimed a first win over Richard Bloomfield in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-01-21 | Great Britain F2 | R32 | hard | Richard Bloomfield | 6-3 6-0 |
| 2008-01-14 | Great Britain F1 | QF | hard | Richard Bloomfield | 6-0 6-4 |
| 2003-09-29 | Great Britain F11 | R32 | hard | Richard Bloomfield | 6-4 6-4 |
| 2002-08-05 | Great Britain F5 | R16 | hard | Richard Bloomfield | 6-3 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.