Round: 44 Ground: Hardcourt outdoor
| ATP Cincinnati Qual | 2016/08/13 19:25 | Jiri Vesely v Tim Smyczek | 6-4,6-2 |
| ATP Washington | 2016/07/18 20:00 | James Duckworth v Tim Smyczek | 7-5,6-1 |
| Challenger Winnipeg | 2016/07/14 15:35 | Tim Smyczek v Daniel Nguyen | 2-6,3-6 |
| Challenger Winnipeg | 2016/07/11 15:00 | Tim Smyczek v Kevin Kylar | 6-1,6-1 |
| Wimbledon Qual | 2016/06/22 12:15 | Tim Smyczek v Hiroki Moriya | 1-6,6-3,4-6 |
| Wimbledon Qual | 2016/06/20 18:05 | Tim Smyczek v Ilya Ivashka | 7-6,6-2 |
| French Open Qual | 2016/05/16 15:25 | Tim Smyczek v Adrian Ungur | 2-6,7-6,3-6 |
| Challenger Bordeaux | 2016/05/09 15:00 | Tim Smyczek v Quentin Halys | 2-6,3-6 |
| Challenger Astana 2 | 2016/07/28 09:15 | Ilya Ivashka v Alexander Kudryavtsev | 4-6,6-2,6-0 |
| Challenger Astana 2 | 2016/07/26 08:25 | Timur Khabibulin v Alexander Kudryavtsev | 0-6,4-6 |
| Wimbledon | 2016/06/28 10:30 | Yen-Hsun Lu v Alexander Kudryavtsev | 6-4,6-1,6-4 |
| Wimbledon Qual | 2016/06/24 12:55 | Adam Pavlasek v Alexander Kudryavtsev | 3-6,2-6,1-6 |
| Wimbledon Qual | 2016/06/22 13:20 | Daniel Nguyen v Alexander Kudryavtsev | 4-6,3-6 |
| Wimbledon Qual | 2016/06/21 11:10 | Alexander Kudryavtsev v Marco Chiudinelli | 7-5,3-6,6-3 |
| French Open Qual | 2016/05/16 16:25 | Alexander Kudryavtsev v Axel Michon | 3-6,5-7 |
| Challenger Zhuhai | 2016/03/11 04:50 | Alexander Kudryavtsev v Jordan Thompson | 3-6,0-6 |