Stadium: Court 9 Round: 44 Ground: Hardcourt outdoor
| Challenger Koblenz | 2018/01/18 17:00 | Nicola Kuhn v Sergiy Stakhovsky | 4-6,3-6 |
| Challenger Segovia | 2019/08/04 16:00 | Pavel Kotov v Nicola Kuhn | 2-6,6-7 |
| Challenger Segovia | 2019/08/03 15:55 | Nicola Kuhn v Markus Eriksson | 6-2,6-2 |
| Challenger Segovia | 2019/08/02 16:45 | Nicola Kuhn v Altug Celikbilek | 7-5,6-4 |
| Challenger Segovia | 2019/08/01 17:55 | Nicola Kuhn v Illya Marchenko | 7-6,6-1 |
| Challenger Segovia | 2019/07/30 16:00 | Nicola Kuhn v Nicolas Barrientos | 6-4,6-3 |
| Challenger Amersfoort | 2019/07/17 08:00 | Nicola Kuhn v Ivan Gakhov | 5-7,6-4,3-6 |
| Challenger Braunschweig | 2019/07/08 11:00 | Nicola Kuhn v Mats Moraing | 3-6,6-2,5-7 |
| Challenger Ludwigshafen | 2019/07/03 13:00 | Nicola Kuhn v Andrej Martin | 5-7,6-4,3-6 |
| Challenger Portoroz | 2019/08/15 16:15 | Zdenek Kolar v Sergiy Stakhovsky | 6-2,3-6,6-3 |
| Challenger Portoroz | 2019/08/14 16:00 | Alessandro Bega v Sergiy Stakhovsky | 1-6,5-7 |
| ATP Los Cabos | 2019/07/28 01:20 | Danilo Petrovic v Sergiy Stakhovsky | 6-4,7-6 |
| Challenger Binghamton | 2019/07/24 19:00 | Alex Rybakov v Sergiy Stakhovsky | 7-6,4-6,7-6 |
| ATP Newport | 2019/07/16 16:50 | Ramkumar Ramanathan v Sergiy Stakhovsky | 5-7,7-6,6-2 |
| Challenger Recanati | 2019/07/04 17:00 | Viktor Galovic v Sergiy Stakhovsky | 5-7,6-3,6-3 |
| Challenger Recanati | 2019/07/03 19:05 | Illya Marchenko v Sergiy Stakhovsky | 6-7,6-3,5-7 |
| Wimbledon | 2019/06/26 12:25 | Andrew Harris v Sergiy Stakhovsky | 3-6,6-3,6-3 |