| ITF Turkey F23 | 2014/07/01 08:00 | Tobias Simon v Markos Kalovelonis | 4-6,6-7 |
| ITF Turkey F22 | 2014/06/24 08:00 | Tobias Simon v Cem Ilkel | 3-6,3-6 |
| ITF Turkey F21 | 2014/06/19 08:00 | Cem Ilkel v Tobias Simon | 6-3,6-4 |
| ITF Turkey F21 | 2014/06/17 09:30 | Tobias Simon v Altug Celikbilek | 7-6,6-4 |
| ITF Bulgaria F1 | 2014/06/12 09:55 | Juan Sebastian Gomez v Tobias Simon | 7-6,6-0 |
| ITF Bulgaria F1 | 2014/06/11 10:55 | Tobias Simon v Teodor-Dacian Craciun | 6-3,6-3 |
| ITF Tunisia F2 | 2014/05/20 12:10 | Tobias Simon v Claudio Grassi | 3-6,4-6 |
| ATP Munich Qual | 2014/04/27 09:00 | Tobias Simon v Ricardas Berankis | 6-7,3-6 |
| ITF Austria F4 | 2014/07/14 11:40 | Tomislav Ternar v Matteo Donati | 4-6,3-6 |
| ITF Austria F3 | 2014/07/09 08:40 | Matteo Donati v Antonio Sancic | 4-6,6-3,6-7 |
| Challenger Todi Qual | 2014/06/30 14:40 | Riccardo Sinicropi v Matteo Donati | 2-6,2-6 |
| Challenger Milan | 2014/06/16 15:40 | Matteo Donati v Marco Trungelliti | 4-6,4-6 |
| Challenger Caltanissetta | 2014/06/09 15:00 | Mate Delic v Matteo Donati | 6-7,7-6,6-1 |
| Challenger Vicenza | 2014/05/30 13:15 | Norbert Gombos v Matteo Donati | 6-0,6-2 |
| Challenger Vicenza | 2014/05/29 15:00 | Matteo Donati v Gonzalo Lama | 6-7,6-4,6-2 |
| Challenger Vicenza | 2014/05/27 13:20 | Giovanni Lapentti v Matteo Donati | 6-7,3-6 |