Stadium: Court Central Round: 26 Ground: Hardcourt outdoor
| Challenger Andria | 2018/11/20 17:45 | Matteo Viola v Sergiy Stakhovsky | 1-6,5-7 |
| Challenger Segovia | 2018/07/31 14:10 | Sergiy Stakhovsky v Matteo Viola | 3-6,6-2,6-7 |
| Challenger Portoroz | 2017/08/08 14:20 | Matteo Viola v Sergiy Stakhovsky | 6-7,2-6 |
| ATP Mallorca | 2021/06/19 16:30 | Matteo Viola v Joao Sousa | 4-6,4-6 |
| Challenger Aix en Provence | 2021/06/15 16:25 | Elias Ymer v Matteo Viola | 6-4,7-6 |
| Challenger Nottingham | 2021/06/06 18:30 | Igor Sijsling v Matteo Viola | 6-7,6-1,6-0 |
| ATP Parma | 2021/05/23 12:55 | Mikael Ymer v Matteo Viola | 6-4,3-6,6-0 |
| ATP Parma | 2021/05/22 12:50 | Evgeny Karlovskiy v Matteo Viola | 5-7,7-5,5-7 |
| Challenger Biella | 2021/05/17 14:55 | Matteo Viola v Alexandre Muller | 6-4,3-6,1-6 |
| Challenger Zagreb | 2021/05/09 11:10 | Emilio Gomez v Matteo Viola | 7-5,6-7,6-1 |
| Challenger Biella | 2021/05/03 08:30 | Maximilian Marterer v Matteo Viola | 6-3,7-5 |
| Challenger Porto | 2021/06/28 14:50 | Sergiy Stakhovsky v Go Soeda | 2-6,6-2,7-6 |
| Wimbledon | 2021/06/23 14:15 | Gregoire Barrere v Sergiy Stakhovsky | 7-5,6-3 |
| Wimbledon | 2021/06/22 14:50 | Sergiy Stakhovsky v Go Soeda | 6-3,7-6 |
| ATP Halle | 2021/06/12 15:10 | Sergiy Stakhovsky v Arthur Rinderknech | 4-6,4-6 |
| ATP Stuttgart | 2021/06/07 12:30 | Sergiy Stakhovsky v Peter Gojowczyk | 1-6,6-7 |
| French Open | 2021/05/26 11:55 | Taro Daniel v Sergiy Stakhovsky | 6-1,6-4 |
| French Open | 2021/05/25 08:30 | Joao Domingues v Sergiy Stakhovsky | 5-7,4-6 |
| Challenger Prague | 2021/05/06 10:00 | Sergiy Stakhovsky v Sumit Nagal | 6-4,1-6,4-6 |