Stadium: Court 5 Round: 27 Ground: Clay
| ITF M25 Prague | 2023/05/18 13:00 | Goncalo Oliveira v Hynek Barton | 6-3,7-6 |
| ITF M25 Prague | 2023/05/17 11:10 | Goncalo Oliveira v Filip Apltauer | 6-4,6-2 |
| ITF M15 Alaminos-Larnaca | 2023/05/11 08:00 | Pietro Marino v Goncalo Oliveira | 2-6,6-7 |
| ITF M15 Alaminos-Larnaca | 2023/05/10 07:00 | Alexandros Skorilas v Goncalo Oliveira | 1-6,1-6 |
| ITF M25 Nottingham | 2023/05/05 09:00 | Goncalo Oliveira v Jules Marie | 4-6,5-7 |
| ITF M25 Nottingham | 2023/05/04 13:55 | Goncalo Oliveira v Louis Bowden | 6-4,6-1 |
| ITF M25 Nottingham | 2023/05/02 10:10 | Goncalo Oliveira v Millen Hurrion | 6-4,6-4 |
| ITF M25 Santa Margherita | 2023/04/19 09:55 | Niccolo Baroni v Goncalo Oliveira | 3-6,5-7 |
| ITF M25 Prague | 2023/05/18 11:00 | Andrew Paulson v Akira Santillan | 2-6,6-3,6-4 |
| ITF M25 Prague | 2023/05/16 12:10 | Andrew Paulson v Stuart Parker | 6-2,3-6,6-3 |
| Challenger Prague Qual | 2023/05/07 11:45 | Bor Artnak v Andrew Paulson | 4-6,6-3,6-4 |
| Challenger Prague | 2023/05/03 12:00 | Dalibor Svrcina v Andrew Paulson | 6-1,3-6,6-0 |
| Challenger Prague | 2023/05/01 11:35 | Ryan Peniston v Andrew Paulson | 6-2,5-7,1-6 |
| Challenger Ostrava | 2023/04/23 09:55 | Khumoyun Sultanov v Andrew Paulson | 6-3,6-2 |
| Challenger Bengaluru | 2023/02/19 05:30 | Mukund Sasikumar v Andrew Paulson | 6-1,6-4 |
| Challenger Chennai | 2023/02/13 06:45 | Andrew Paulson v Petr Nouza | 3-6,4-6 |