Andrew Painter defeated Toby Mitchell 4-6 6-4 7-5 in the Great Britain 3 Masters 3 round of 16 on grass. The upset overturned the form book — Toby Mitchell came in leading the head-to-head 3–0. Andrew Painter claimed a first win over Toby Mitchell in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-10-28 | Australia F1 | R16 | clay | Toby Mitchell | 6-1 6-2 |
| 1998-04-07 | New Zealand Masters 2 | R16 | hard | Toby Mitchell | 6-3 6-4 |
| 1997-05-10 | Australia 2 Masters 2 | QF | hard | Toby Mitchell | 5-7 7-6 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.