David Sherwood defeated Ian Flanagan 6-2 6-2 in the Great Britain F7 round of 32 on hard. The upset overturned the form book — Ian Flanagan came in leading the head-to-head 1–0. David Sherwood claimed a first win over Ian Flanagan in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-01-30 | Great Britain 1 4 | R16 | hard | Ian Flanagan | 6-4 3-6 6-3 |
Averages over each player's completed matches in the selected window (2 vs 3). ATP, WTA & Challenger.
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About