Round: 1 Ground: Hardcourt indoor
| Wimbledon | 2016/06/27 11:55 | Janko Tipsarevic v Gilles Simon | 6-4,4-6,5-7,3-6 |
| French Open | 2016/05/23 11:35 | Milos Raonic v Janko Tipsarevic | 6-3,6-2,7-6 |
| ATP Geneva | 2016/05/16 13:20 | Federico Delbonis v Janko Tipsarevic | 6-1,7-6 |
| Challenger Heilbronn | 2016/05/10 11:55 | Janko Tipsarevic v Carlos Berlocq | 5-7,3-6 |
| Challenger Ostrava | 2016/04/26 12:15 | Janko Tipsarevic v Hans Podlipnik-Castillo | 7-6,3-6,6-4 |
| US Open | 2015/09/01 19:40 | Janko Tipsarevic v Guillermo Garcia-Lopez | 6-7,6-4,6-4,3-6,1-6 |
| ATP Montreal | 2015/08/11 19:00 | Roberto Bautista-Agut v Janko Tipsarevic | 6-3,6-4 |
| Wimbledon | 2015/06/29 10:30 | Janko Tipsarevic v Marcel Granollers | 3-6,4-6,2-6 |
| Wimbledon | 2016/06/27 10:30 | Kyle Edmund v Adrian Mannarino | 2-6,5-7,4-6 |
| French Open | 2016/05/25 12:30 | John Isner v Kyle Edmund | 6-4,6-4,6-4 |
| French Open | 2016/05/23 16:30 | Nikoloz Basilashvili v Kyle Edmund | 6-7,7-6,5-7,1-6 |
| Challenger Rome | 2016/05/07 14:00 | Filip Krajinovic v Kyle Edmund | 6-7,0-6 |
| Challenger Rome | 2016/05/06 13:00 | Filippo Volandri v Kyle Edmund | 1-6,4-6 |
| Challenger Rome | 2016/05/05 11:30 | Blaz Rola v Kyle Edmund | 4-6,6-3,0-6 |
| Challenger Rome | 2016/05/04 12:45 | Kevin Krawietz v Kyle Edmund | 3-6,4-6 |
| Challenger Rome | 2016/05/02 12:30 | Jurgen Zopp v Kyle Edmund | 4-6,3-6 |