Round: 45 Ground: Clay
| Challenger - San Benedetto | 2016/07/11 18:40 | Nils Langer v Ivan Nedelko | 3-6,6-1,2-6 |
| Challenger Marburg | 2016/06/28 10:40 | Nils Langer v Daniel Gimeno-Traver | 6-7,7-5,1-6 |
| Wimbledon Qual | 2016/06/21 11:15 | Igor Sijsling v Nils Langer | 6-2,6-4 |
| Challenger Poprad Tatry | 2016/06/14 11:20 | Nils Langer v Andrej Martin | 5-7,7-6,2-6 |
| French Open Qual | 2016/05/17 08:00 | Nils Langer v Andrej Martin | 3-6,1-6 |
| ATP Munich Qual | 2016/04/24 12:45 | Nils Langer v Cedrik-Marcel Stebe | 6-2,6-7,4-6 |
| ATP Munich Qual | 2016/04/23 13:05 | Mirza Basic v Nils Langer | 4-6,3-6 |
| Challenger - Zhuhai | 2016/03/08 05:30 | Nils Langer v Kevin Krawietz | 6-7,3-6 |
| Challenger Milan Qual | 2016/06/23 16:35 | Daniel Gimeno-Traver v Filippo Volandri | 6-2,2-6,6-0 |
| Challenger Milan Qual | 2016/06/21 15:35 | Filippo Volandri v Lorenzo Sonego | 6-3,6-3 |
| Challenger - Perugia | 2016/06/15 12:05 | Rogerio Dutra Silva v Filippo Volandri | 6-2,7-6 |
| Challenger - Perugia | 2016/06/13 15:35 | Filippo Volandri v Andrea Arnaboldi | 6-4,6-7,6-4 |
| Challenger Caltanissetta | 2016/06/07 16:35 | Laslo Djere v Filippo Volandri | 7-6,6-7,6-2 |
| Challenger - Vicenza | 2016/05/26 15:30 | Filippo Volandri v Nicolas Kicker | 2-6,1-6 |
| Challenger - Vicenza | 2016/05/24 17:10 | Filippo Volandri v Marton Fucsovics | 7-6,6-2 |
| French Open Qual | 2016/05/16 09:35 | Kenny de Schepper v Filippo Volandri | 6-3,7-6 |