Round: 25 Ground: Clay
| ITF Finland F3 Qual | 2016/08/13 22:00 | Barros, Emmanuel v Wennakoski, Max | 1-6,4-6 |
| ITF Finland F2 | 2016/08/09 10:25 | Wennakoski, Max v Griekspoor, Kevin | 4-6,2-6 |
| ITF Finland F2 Qual | 2016/08/07 15:00 | Gohlke, Delf v Wennakoski, Max | 4-6,2-6 |
| ITF Finland F2 Qual | 2016/08/06 10:00 | Pollanen, Herkko v Wennakoski, Max | 4-6,7-5,2-6 |
| ITF USA F19 Qual | 2016/06/13 16:00 | Kopinski, Tim v Wennakoski, Max | 6-4,6-4 |
| ITF USA F19 Qual | 2016/06/12 16:00 | Krustev, Victor v Wennakoski, Max | 5-7,0-6 |
| ITF Canada F1 Qual | 2016/02/28 15:00 | Smith, Roy v Wennakoski, Max | 2-6,1-6 |
| ITF Dominican Republic F3 | 2015/12/15 15:50 | Torebko, Peter v Wennakoski, Max | 2-6,6-4,6-2 |
| ITF Georgia F2 | 2016/08/05 07:00 | Dowson, Dan v Thomas Fancutt | 6-7,6-3,6-4 |
| ITF Georgia F2 | 2016/08/04 06:00 | Tsivadze, George v Thomas Fancutt | 4-6,6-3,3-6 |
| ITF Georgia F2 | 2016/08/02 06:00 | Oleg Prihodko v Thomas Fancutt | 2-6,3-6 |
| ITF China F13 | 2016/07/23 02:30 | Issei Okamura v Thomas Fancutt | 2-6,4-6 |
| ITF China F13 | 2016/07/22 02:30 | Kuan-Yi Lee v Thomas Fancutt | 6-7,6-3,2-6 |
| ITF China F13 | 2016/07/21 02:30 | Thomas Fancutt v He, Yecong | 6-3,6-2 |
| ITF China F13 | 2016/07/20 05:05 | Thomas Fancutt v Zhong, Su Hao | 6-2,6-2 |
| ITF China F13 | 2016/07/19 06:55 | Mukund Sasikumar v Thomas Fancutt | 5-7,3-6 |