Pavel Shumeiko defeated Peter Bothwell 3-6 6-4 6-3 in the M15 Sintra 2 round of 32 on hard. The upset overturned the form book — Peter Bothwell came in leading the head-to-head 2–0, but Pavel Shumeiko had been the form player, winning 4 of their last 10 on hard. Pavel Shumeiko claimed a first win over Peter Bothwell in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-05-17 | M15 Heraklion 2 | QF | hard | Peter Bothwell | 6-4 6-7(5) 6-3 |
| 2019-05-02 | M15 Tbilisi 1 | R16 | hard | Peter Bothwell | 7-6(7) 3-6 6-2 |