Ivan Sergeyev defeated Illya Beloborodko 6-1 7-6 in the M15 Irpin 3 round of 32 on clay. Ivan Sergeyev extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2024-09-24 | M15 Trnava 1 | Q16 | hard | Illya Beloborodko | 7-6(6) 6-3 |
| 2020-08-31 | M15 Novomoskovsk 1 | Q16 | clay | Ivan Sergeyev | 6-3 4-6 10-5 |