Round: 23 Ground: Clay
| French Open Qual | 2016/05/19 14:50 | Adrian Ungur v Frances Tiafoe | 4-6,6-2,6-4 |
| French Open Qual | 2016/05/18 11:45 | Adrian Ungur v Marton Fucsovics | 6-4,6-2 |
| French Open Qual | 2016/05/16 15:25 | Tim Smyczek v Adrian Ungur | 2-6,7-6,3-6 |
| Challenger Rome | 2016/05/02 12:00 | Adrian Ungur v Filip Krajinovic | 6-3,0-6,3-6 |
| ATP Monte Carlo Qual | 2016/04/09 13:05 | Adrian Ungur v Jan-Lennard Struff | 3-6,6-7 |
| Davis Cup | 2016/03/06 12:00 | Adrian Ungur v Blaz Rola | 3-6,4-6 |
| Davis Cup | 2016/03/04 14:35 | Adrian Ungur v Grega Zemlja | 4-6,4-6,6-3,7-6,6-4 |
| Challenger Wroclaw | 2016/02/15 15:10 | Adrian Ungur v Konstantin Kravchuk | 2-6,3-6 |
| French Open Qual | 2016/05/20 10:15 | Igor Sijsling v Kenny de Schepper | 3-6,2-6 |
| French Open Qual | 2016/05/18 13:40 | Igor Sijsling v Grega Zemlja | 6-4,6-0 |
| French Open Qual | 2016/05/16 09:25 | Igor Sijsling v Franko Skugor | 6-7,7-6,6-3 |
| Challenger Heilbronn | 2016/05/13 12:00 | Nikoloz Basilashvili v Igor Sijsling | 6-2,3-6,6-4 |
| Challenger Heilbronn | 2016/05/12 15:30 | Maximilian Marterer v Igor Sijsling | 2-6,4-6 |
| Challenger Heilbronn | 2016/05/10 14:20 | Adrian Menendez-Maceiras v Igor Sijsling | 1-6,6-7 |
| ATP Munich | 2016/04/28 09:00 | Igor Sijsling v Jozef Kovalik | 3-6,4-6 |
| ATP Munich | 2016/04/26 10:45 | Marco Cecchinato v Igor Sijsling | 2-6,4-6 |