Milos Sekulic defeated Vladimir Ivanov 6-3 6-4 in the Estonia F3 round of 32 on hard. The upset overturned the form book — Vladimir Ivanov came in leading the head-to-head 3–0. Milos Sekulic claimed a first win over Vladimir Ivanov in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2016-11-07 | Estonia F4 | R32 | hard | Vladimir Ivanov | 3-6 7-5 7-6(4) |
| 2012-08-20 | Finland F3 | QF | clay | Vladimir Ivanov | 6-3 6-4 |
| 2012-08-06 | Finland F1 | F | clay | Vladimir Ivanov | 6-4 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.