| ATP Hamburg Qual | 2014/07/12 10:50 | Demian Raab v Marsel Ilhan | 4-6,4-6 |
| ITF Poland F2 | 2014/06/11 09:20 | Adam Majchrowicz v Demian Raab | 7-5,6-3 |
| ITF Poland F2 | 2014/06/10 10:20 | Demian Raab v Arthur Surreaux | 6-4,7-5 |
| ITF Hungary F1 | 2014/06/03 09:00 | Patrik Rosenholm v Demian Raab | 6-4,6-4 |
| ITF Romania F2 | 2014/05/20 07:00 | Dragos Dima v Demian Raab | 6-0,6-1 |
| ITF Italy F12 | 2014/04/30 09:55 | Demian Raab v Luca Vanni | 4-6,6-7 |
| ITF Romania F13 | 2014/08/30 07:30 | Filippo Leonardi v Frederico Ferreira Silva | 3-6,3-6 |
| ITF Romania F13 | 2014/08/29 09:45 | Petru-Alexandru Luncanu v Filippo Leonardi | 2-6,2-6 |
| ITF Romania F13 | 2014/08/28 08:00 | Filippo Leonardi v Luca George Tatomir | 6-4,6-4 |
| ITF Romania F13 | 2014/08/26 09:05 | Filippo Leonardi v Dragos Dima | 6-3,6-3 |
| ITF Italy F24 | 2014/07/23 11:00 | Filippo Leonardi v Matteo Trevisan | 6-7,1-6 |
| ITF Italy F24 | 2014/07/21 13:00 | Filippo Leonardi v Antonio Massara | 6-3,7-6 |
| ITF Italy F23 | 2014/07/15 11:25 | Filippo Leonardi v Marco Bortolotti | 6-3,6-2 |
| ITF Italy F18 | 2014/06/10 10:40 | Edoardo Eremin v Filippo Leonardi | 6-1,7-5 |