Stadium: Center Court Round: 25 Ground: Hardcourt indoor
| Challenger Scheveningen | 2017/07/19 14:20 | Simone Bolelli v Sergiy Stakhovsky | 6-4,3-6,6-3 |
| Challenger Orleans | 2018/09/28 16:30 | Sergiy Stakhovsky v Aljaz Bedene | 6-7,4-6 |
| Challenger Orleans | 2018/09/26 20:45 | Quentin Halys v Sergiy Stakhovsky | 5-7,6-3,6-7 |
| Challenger Orleans | 2018/09/25 12:30 | Tak Khunn Wang v Sergiy Stakhovsky | 5-7,6-7 |
| ATP Metz | 2018/09/16 14:00 | Sergiy Stakhovsky v Maxime Janvier | 3-6,4-6 |
| Davis Cup | 2018/09/15 10:00 | Sergiy Stakhovsky v Joao Sousa | 6-2,4-6,6-4 |
| Davis Cup | 2018/09/14 11:30 | Sergiy Stakhovsky v Pedro Sousa | 6-3,6-2 |
| Challenger Cassis | 2018/09/04 13:05 | Oscar Otte v Sergiy Stakhovsky | 7-6,3-6,7-5 |
| Challenger Mallorca | 2018/08/30 09:30 | Kenny de Schepper v Sergiy Stakhovsky | 6-2,6-4 |
| 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 |
| Challenger Padova | 2018/07/25 17:00 | Edoardo Eremin v Simone Bolelli | 6-1,3-6,6-2 |