Stadium: Center Court Round: 26 Ground: Hardcourt indoor
| Challenger Ortisei | 2018/10/09 13:25 | Jaume Munar v Kirill Kivattsev | 3-6,6-7 |
| Challenger Ortisei | 2018/10/08 09:45 | Kirill Kivattsev v Fabrizio Ornago | 4-6,6-3,6-4 |
| Challenger Ortisei | 2018/10/07 12:25 | Viktor Galovic v Kirill Kivattsev | 5-7,7-6,6-7 |
| Challenger Ortisei | 2018/10/06 15:30 | Kirill Kivattsev v Francesco Vilardo | 6-3,3-6,6-3 |
| ITF Turkey F29 | 2018/09/30 07:30 | Riccardo Bonadio v Kirill Kivattsev | 6-1,6-2 |
| ITF Turkey F29 | 2018/09/29 07:00 | Nikolas Sanchez Izquierdo v Kirill Kivattsev | 4-6,2-6 |
| ITF Turkey F29 | 2018/09/28 08:30 | Claudio Fortuna v Kirill Kivattsev | 5-7,2-6 |
| ITF Turkey F29 | 2018/09/26 09:20 | Kirill Kivattsev v Thomas Statzberger | 7-6,6-2 |
| Challenger Ortisei | 2018/10/09 17:50 | Sergiy Stakhovsky v Simone Bolelli | 6-7,3-6 |
| Challenger Sibiu | 2018/09/20 10:05 | Simone Bolelli v Jelle Sels | 6-7,3-6 |
| Challenger Sibiu | 2018/09/18 10:00 | Simone Bolelli v Jeremy Jahn | 6-4,6-4 |
| Challenger Szczecin | 2018/09/12 12:20 | Simone Bolelli v Rogerio Dutra Silva | 2-6,4-6 |
| Challenger Szczecin | 2018/09/10 13:50 | Simone Bolelli v Kenny de Schepper | 7-5,4-6,6-2 |
| US Open | 2018/08/23 15:00 | Donald Young v Simone Bolelli | 0-6,6-4,6-2 |
| US Open | 2018/08/21 22:50 | Maximilian Neuchrist v Simone Bolelli | 5-7,7-5,5-7 |
| Challenger Pullach | 2018/08/06 13:05 | Simone Bolelli v Sebastian Ofner | 3-6,4-6 |