Round: 25 Ground: Clay
| ATP - Hamburg - Qualifikation | 2016/07/10 10:00 | Daniil Medvedev v Jan Mertl | 6-4,6-2 |
| ATP - Hamburg - Qualifikation | 2016/07/09 10:00 | Roberto Ortega-Olmedo v Jan Mertl | 4-6,2-6 |
| ITF - Tschechien F4 | 2016/06/30 13:30 | Zdenek Kolar v Jan Mertl | 7-5,6-2 |
| ITF - Tschechien F4 | 2016/06/29 10:30 | Joao Pedro Sorgi v Jan Mertl | 1-6,4-6 |
| ITF - Tschechien F4 | 2016/06/28 10:30 | Lukas Vejvara v Jan Mertl | 2-6,2-6 |
| ITF - Niederlande F2 | 2016/06/23 13:15 | Tim Van Rijthoven v Jan Mertl | 6-3,3-6,6-4 |
| ITF - Niederlande F2 | 2016/06/22 08:00 | Tom Schonenberg v Jan Mertl | 4-6,2-6 |
| Challenger - Poprad Tatry | 2016/06/14 11:35 | Jan Mertl v Gerald Melzer | 1-6,2-6 |
| Davis Cup | 2016/07/16 14:00 | Nicolas Jarry v Santiago Giraldo | 2-6,4-6,3-6 |
| Wimbledon | 2016/06/27 16:10 | Santiago Giraldo v Gilles Müller | 6-4,7-6,6-7,3-6,13-15 |
| Challenger - Perugia | 2016/06/13 10:05 | Blaz Rola v Santiago Giraldo | 6-3,3-6,6-3 |
| Challenger - Caltanissetta | 2016/06/08 17:20 | Santiago Giraldo v Matteo Donati | 2-6,6-3,6-7 |
| Challenger - Caltanissetta | 2016/06/06 13:40 | Santiago Giraldo v Lorenzo Giustino | 6-4,6-1 |
| French Open | 2016/05/24 15:05 | Paul-Henri Mathieu v Santiago Giraldo | 6-4,6-7,6-4,1-6,6-3 |
| ATP - Madrid | 2016/05/03 10:00 | Santiago Giraldo v Roberto Bautista-Agut | 3-6,5-7 |
| ATP - Madrid - Qualifikation | 2016/05/01 09:00 | Dusan Lajovic v Santiago Giraldo | 4-6,3-6 |