Jack Gibbens defeated Sacha Modica 6-3 7-5 in the M15 Monastir 17 round of 32 on hard. The upset overturned the form book — Sacha Modica came in leading the head-to-head 2–0. Jack Gibbens claimed a first win over Sacha Modica in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2020-10-18 | M15 Monastir 16 | Q32 | hard | Sacha Modica | 7-6(5) 6-2 |
| 2020-09-15 | M15 Monastir 11 | Q16 | hard | Sacha Modica | 6-3 6-2 |