Stadium: Court Central Round: 27 Ground: Clay
| Challenger Porto | 2021/06/30 10:00 | Peter Polansky v Goncalo Oliveira | 6-7,4-6 |
| Challenger Porto | 2021/06/29 10:00 | Goncalo Oliveira v Nuno Borges | 6-1,6-2 |
| Challenger Milan | 2021/06/20 10:30 | Goncalo Oliveira v Nerman Fatic | 6-4,5-7,3-6 |
| Challenger Prostejov | 2021/06/14 10:25 | Goncalo Oliveira v Michael Vrbensky | 3-6,6-2,4-6 |
| Challenger Little Rock | 2021/06/05 16:00 | Emilio Gomez v Goncalo Oliveira | 6-4,6-2 |
| Challenger Little Rock | 2021/06/03 17:50 | Mukund Sasikumar v Goncalo Oliveira | 6-4,4-6,2-6 |
| Challenger Little Rock | 2021/05/31 21:00 | Goncalo Oliveira v Ryan Harrison | 7-5,7-6 |
| Challenger Oeiras | 2021/05/26 14:45 | Goncalo Oliveira v Timofey Skatov | 3-6,1-6 |
| Challenger Porto | 2021/06/30 13:45 | Matteo Viola v Sergiy Stakhovsky | 2-6,6-4,5-7 |
| 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 |