Stadium: Stadium Round: 25 Ground: Hardcourt outdoor
| Challenger - Oeiras | 2021/05/26 14:45 | Goncalo Oliveira v Timofey Skatov | 3-6,1-6 |
| Challenger - Oeiras | 2021/05/25 13:00 | Pedro Cachin v Goncalo Oliveira | 4-6,7-5,6-7 |
| Challenger - Oeiras | 2021/05/17 09:30 | Emilio Gomez v Goncalo Oliveira | 6-2,3-6,6-4 |
| Challenger - Oeiras | 2021/05/16 12:30 | Goncalo Oliveira v Maxime Janvier | 6-3,6-4 |
| Challenger - Oeiras | 2021/04/09 14:55 | Goncalo Oliveira v Tiago Cacao | 7-5,6-2 |
| Challenger - Oeiras | 2021/04/08 15:50 | Oscar Otte v Goncalo Oliveira | 4-6,6-4,3-6 |
| Challenger - Oeiras | 2021/04/06 15:10 | Riccardo Bonadio v Goncalo Oliveira | 6-7,5-7 |
| Challenger - Oeiras | 2021/03/31 11:20 | Marco Trungelliti v Goncalo Oliveira | 6-1,6-3 |
| Challenger - Tallahassee | 2021/04/21 19:00 | Ryan Harrison v Michael Mmoh | 4-6,3-6 |
| Challenger - Tallahassee | 2021/04/20 14:00 | Ryan Harrison v Donald Young | 2-6,6-3,6-3 |
| ATP - Delray Beach | 2021/01/07 19:30 | Gianluca Mager v Ryan Harrison | 3-6,6-1,6-4 |
| ATP - Acapulco | 2020/02/23 01:00 | Daniel Altmaier v Ryan Harrison | 6-2,6-3 |
| ATP - Delray Beach | 2020/02/19 17:30 | Soonwoo Kwon v Ryan Harrison | 6-4,3-6,7-6 |
| ATP - Delray Beach | 2020/02/17 17:45 | Ryan Harrison v Damir Dzumhur | 6-3,6-2 |
| Challenger - Cleveland | 2020/02/13 19:55 | Geoffrey Blancaneaux v Ryan Harrison | 6-3,3-6,6-2 |
| Challenger - Cleveland | 2020/02/13 00:05 | Ryan Harrison v Sebastian Ofner | 6-3,6-7,6-3 |