Fred Simonsson defeated Milos Sekulic 7-5 6-1 in the Sweden F3 round of 32 on hard. Fred Simonsson extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2016-09-26 | Sweden F4 | R32 | hard | Milos Sekulic | 2-6 6-1 6-1 |
| 2013-10-13 | Stockholm | Q16 | hard | Milos Sekulic | 6-1 6-2 |
| 2013-07-22 | Denmark F2 | R32 | clay | Fred Simonsson | 7-6(6) 6-0 |
| 2012-10-01 | Sweden F7 | R16 | hard | Fred Simonsson | 6-3 4-6 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.