Stadium: Grandstand Round: 23 Ground: Hardcourt outdoor
| Czechia Extraliga | 2016/12/19 09:00 | Karen Khachanov v Andrej Martin | 6-0,6-3 |
| Czechia Extraliga | 2016/12/17 10:00 | Karen Khachanov v Petr Michnev | 3-6,2-6 |
| ATP Vienna | 2016/10/28 11:00 | Ivo Karlovic v Karen Khachanov | 6-7,7-6,6-3 |
| ATP Vienna | 2016/10/26 18:55 | Karen Khachanov v Nikoloz Basilashvili | 6-2,7-5 |
| ATP Vienna | 2016/10/24 11:00 | Andreas Seppi v Karen Khachanov | 4-6,4-6 |
| ATP Moscow | 2016/10/19 14:15 | Karen Khachanov v Damir Dzumhur | 6-3,6-7,4-6 |
| ATP Shanghai Qual | 2016/10/08 04:00 | Karen Khachanov v Mischa Zverev | 6-4,4-6,4-6 |
| Others | 2016/10/02 08:30 | Albert Ramos-Vinolas v Karen Khachanov | 7-6,6-7,3-6 |
| Challenger Montevideo | 2016/11/20 21:00 | Rogerio Dutra Silva v Diego Schwartzman | 4-6,1-6 |
| Challenger Montevideo | 2016/11/18 18:30 | Nicolas Kicker v Diego Schwartzman | 4-6,6-7 |
| Challenger Montevideo | 2016/11/16 23:00 | Tomas Lipovsek Puches v Diego Schwartzman | 1-6,3-6 |
| Challenger Montevideo | 2016/11/14 23:30 | Maximiliano Estevez v Diego Schwartzman | 0-6,1-6 |
| ATP Antwerp | 2016/10/23 12:30 | Diego Schwartzman v Richard Gasquet | 6-7,1-6 |
| ATP Antwerp | 2016/10/22 14:30 | David Goffin v Diego Schwartzman | 5-7,6-2,5-7 |
| ATP Antwerp | 2016/10/21 13:45 | Pablo Cuevas v Diego Schwartzman | 6-7,3-6 |
| ATP Antwerp | 2016/10/20 10:00 | Taylor Fritz v Diego Schwartzman | 4-6,4-6 |