Round: 54 Ground: Clay
| ITF Finland F1 | 2016/08/01 14:35 | Sillanpaa, Henrik v Brydolf, Patrik | 3-6,7-6,6-7 |
| ITF Estonia F1 | 2016/07/26 22:00 | Fortuna, Claudio v Sillanpaa, Henrik | 6-2,6-4 |
| ITF Estonia F1 | 2016/07/24 22:00 | Sillanpaa, Henrik v Kosonen, Mika | 3-6,6-3,6-3 |
| Challenger Tampere Qual | 2016/07/17 08:00 | Kiiski, Lauri v Sillanpaa, Henrik | 6-3,6-4 |
| Challenger Tampere Qual | 2016/07/16 11:15 | Sillanpaa, Henrik v Arvidsson, Isak | 1-6,6-3,6-4 |
| ITF Tunisia F11 | 2016/03/23 10:00 | Sillanpaa, Henrik v Vega Hernandez, David | 6-4,6-3 |
| Tunisia F10, Singles Qualifying | 2016/03/15 12:10 | Sillanpaa, Henrik v Sieber, Marc | 2-6,0-6 |
| ITF Tunisia F9 | 2016/03/08 10:20 | Ben Hassen, Ameur v Sillanpaa, Henrik | 0-6,6-2,6-4 |
| ITF Finland F1 | 2016/08/01 09:00 | Jacob Kahoun v Mudge, Robbie | 6-1,4-6,6-7 |
| ITF Germany F8 Qual | 2016/07/18 12:40 | Pel, David v Jacob Kahoun | 6-3,6-2 |
| ITF Germany F8 Qual | 2016/07/17 15:00 | Solanki, Alex v Jacob Kahoun | 3-6,2-6 |
| ITF Germany F8 Qual | 2016/07/17 08:30 | Schommer, Fred Olivier v Jacob Kahoun | 0-6,2-6 |
| ITF Morocco F3 | 2016/03/22 15:35 | Lombe, Harrison v Jacob Kahoun | 6-1,2-6,6-3 |
| ITF Morocco F2 | 2016/03/13 13:00 | Jacob Kahoun v Lopez Perez Fuster, Jorge | 4-6,2-6 |
| ITF Morocco F2 | 2016/03/13 10:00 | Jacob Kahoun v Bellalouna, Mohamed Ali | 6-1,6-1 |
| ITF Morocco F1 | 2016/03/08 10:00 | Schutt, Leon v Jacob Kahoun | 6-4,4-6,6-4 |