Ground: Clay
| ITF Estonia F2 | 2014/07/22 07:00 | Tyurnev, Evgeny v Cayre, Paul | 6-3,1-6,7-6 |
| ITF Estonia F1 | 2014/07/15 09:20 | Cayre, Paul v Alexander Vasilenko | 1-6,6-7 |
| ITF France F14 | 2014/07/11 11:35 | Cayre, Paul v Constant Lestienne | 0-6,0-6 |
| ITF France F14 | 2014/07/08 08:30 | Antoine Walch v Cayre, Paul | 6-7,1-6 |
| France F14, Singles Qualifying | 2014/07/06 10:05 | Cayre, Paul v Crepatte, Baptiste | 6-3,7-5 |
| France F14, Singles Qualifying | 2014/07/05 14:50 | Cayre, Paul v Ruppli, Andrew | 7-5,7-5 |
| ITF France F13 | 2014/07/01 16:00 | Cayre, Paul v Gigounon, Germain | 6-1,4-6,6-4 |
| ITF France F6 Qual | 2014/03/10 15:45 | Penaud, Alexandre v Cayre, Paul | 1-6,4-6 |
| ITF Finland F1 | 2014/08/07 08:00 | Sillanpaa, Henrik v Arneodo, Romain | 6-1,6-4 |
| ITF Finland F1 | 2014/08/06 09:50 | Sillanpaa, Henrik v Gao, Xin | 6-4,6-3 |
| Challenger Tampere | 2014/07/24 11:00 | Sillanpaa, Henrik v Elias Ymer | 4-6,3-6 |
| Challenger Tampere | 2014/07/22 11:20 | Desein, Niels v Sillanpaa, Henrik | 7-6,2-6,4-6 |
| ITF Estonia F1 | 2014/07/15 07:00 | Sillanpaa, Henrik v Eriksson, Markus | 3-6,2-6 |
| ATP Bastad Qual | 2014/07/06 14:35 | Sillanpaa, Henrik v Cervantes, Inigo | 3-6,2-6 |
| ATP Bastad Qual | 2014/07/05 13:30 | Sillanpaa, Henrik v Sekulic, Milos | 6-7,7-5,6-3 |
| ITF Hungary F2 | 2014/06/10 08:00 | Sillanpaa, Henrik v Maximilian Marterer | 6-7,3-6 |