Round: 25 Ground: Hardcourt indoor
| Challenger Genova Qual | 2016/09/05 14:15 | Fred Simonsson v Dino Marcan | 4-6,1-6 |
| Challenger Genova Qual | 2016/09/05 09:25 | Nikola Mektic v Fred Simonsson | 6-7,7-5,6-7 |
| Challenger Genova Qual | 2016/09/04 10:15 | Fred Simonsson v Aliaksandr Bury | 6-3,6-1 |
| ITF Lithuania F1 | 2016/07/22 12:00 | Fred Simonsson v Krisjanis Stabins | 4-6,6-7 |
| ITF Lithuania F1 | 2016/07/21 11:00 | Fred Simonsson v Mikalai Haliak | 6-1,6-3 |
| ITF Lithuania F1 | 2016/07/20 08:00 | Fred Simonsson v Michal Dembek | 4-6,6-4,6-1 |
| ATP Bastad | 2016/07/12 14:05 | Fred Simonsson v Carl Soderlund | 3-6,6-3,6-7 |
| Challenger Bastad Qual | 2016/07/03 11:25 | Prajnesh Gunneswaran v Fred Simonsson | 4-6,7-5,6-3 |
| ITF Russia F7 | 2016/08/31 08:00 | Milos Sekulic v Yannick Mertens | 4-6,1-6 |
| ITF Russia F7 | 2016/08/30 10:15 | Milos Sekulic v Stanislav Skobelev | 7-5,6-0 |
| Challenger Prague 2 | 2016/07/24 09:00 | Matej Vocel v Milos Sekulic | 4-6,6-3,7-6 |
| Challenger Prague 2 | 2016/07/23 09:00 | Dominik Recek v Milos Sekulic | 6-7,4-6 |
| Challenger Tampere | 2016/07/19 07:00 | Aleksandr Nedovyesov v Milos Sekulic | 6-1,6-2 |
| Challenger Tampere Qual | 2016/07/17 11:40 | Milos Sekulic v Sami Huurinainen | 6-1,6-2 |
| Challenger Tampere Qual | 2016/07/16 09:00 | Pauli Partinen v Milos Sekulic | 0-6,3-6 |
| ATP Bastad Qual | 2016/07/10 10:00 | Milos Sekulic v Nikola Cacic | 7-6,5-7,4-6 |