Round: 25 Ground: Clay
| ITF Great Britain F2 | 2015/01/25 10:00 | Daniel Appelgren v Jonathan Gray | 6-3,7-5 |
| ITF Finland F2 | 2016/08/11 10:00 | Ivan Nedelko v Daniel Appelgren | 7-5,7-6 |
| ITF Finland F2 | 2016/08/10 08:00 | Christoffer Solberg v Daniel Appelgren | 4-6,6-7 |
| ITF Finland F2 | 2016/08/09 07:30 | Paul Monteban v Daniel Appelgren | 6-7,1-6 |
| ITF Finland F1 | 2016/08/04 13:00 | Daniel Appelgren v Mikael Torpegaard | 2-6,2-6 |
| ITF Finland F1 | 2016/08/03 12:25 | Daniel Appelgren v Robbie Mudge | 6-1,6-3 |
| ITF Finland F1 | 2016/08/02 13:15 | Daniel Appelgren v Eero Vasa | 6-2,6-4 |
| Challenger Prague 2 | 2016/07/24 11:25 | Hubert Hurkacz v Daniel Appelgren | 6-1,6-7,7-6 |
| ATP Bastad Qual | 2016/07/10 10:00 | Daniel Appelgren v Scott Griekspoor | 4-6,4-6 |
| ITF Finland F2 | 2016/08/10 08:00 | Jonathan Gray v Tallon Griekspoor | 2-6,2-6 |
| ITF Finland F2 | 2016/08/09 09:20 | Tomas Gerini v Jonathan Gray | 3-6,5-7 |
| ITF Finland F2 Qual | 2016/08/07 14:35 | Jonathan Gray v Emil Ruusuvuori | 7-6,6-0 |
| ITF Finland F2 Qual | 2016/08/06 12:30 | Jonathan Gray v Otto Virtanen | 6-4,6-0 |
| ITF Latvia F1 | 2016/08/02 09:10 | Laurynas Grigelis v Jonathan Gray | 7-6,6-0 |
| ITF Estonia F1 | 2016/07/24 22:00 | Jonathan Gray v Alexander Vasilenko | 6-2,4-6,4-6 |
| ITF Belgium F6 | 2016/07/18 10:45 | Jonathan Gray v Jules Okala | 2-6,6-7 |
| ITF Belgium F6 Qual | 2016/07/17 08:00 | Jonathan Gray v Luc Fomba | 6-2,6-3 |