Stadium: Court 2 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Faro | 2019/02/26 11:50 | Oscar Jose Gutierrez v Paul Cayre | 6-3,6-0 |
| ITF M25 Torello | 2023/02/28 10:50 | Xavi Matas Ortega v Paul Cayre | 4-6,2-6 |
| ITF M25 Torello | 2023/02/27 15:00 | Raffael Schaer v Paul Cayre | 4-6,5-7 |
| ITF M25 Torello | 2023/02/27 10:30 | Iker Urribarrens v Paul Cayre | 5-7,2-6 |
| ITF M15 Grenoble | 2023/02/10 14:30 | Nikolay Vylegzhanin v Paul Cayre | 6-2,6-1 |
| ITF M15 Grenoble | 2023/02/09 10:00 | Paul Cayre v Louis Dussin | 7-5,1-6,7-5 |
| ITF M15 Grenoble | 2023/02/08 13:00 | Riccardo Balzerani v Paul Cayre | 2-6,6-1,3-6 |
| ITF M15 Grenoble | 2023/02/06 10:25 | Tom Gentzsch v Paul Cayre | 2-6,6-3,8-10 |
| ITF M15 Grenoble | 2023/02/06 09:00 | Paul Cayre v Simon Reveniau | 6-1,4-6,10-8 |
| Challenger Rovereto | 2023/02/19 12:05 | Alejandro Moro Canas v Oscar Jose Gutierrez | 6-4,6-0 |
| ITF M25 Vila Real de Santo Antonio | 2023/02/16 11:25 | Federico Gaio v Oscar Jose Gutierrez | 4-6,6-4,6-2 |
| ITF M25 Vila Real de Santo Antonio | 2023/02/15 15:20 | Timo Legout v Oscar Jose Gutierrez | 4-6,4-6 |
| Challenger Tenerife | 2023/02/09 13:05 | Stefano Travaglia v Oscar Jose Gutierrez | 6-0,6-0 |
| Challenger Tenerife | 2023/02/07 12:50 | Oscar Jose Gutierrez v Marek Gengel | 1-6,6-0,6-3 |
| Challenger Tenerife Qual | 2023/02/06 15:00 | Oscar Jose Gutierrez v Christian Harrison | 4-6,6-4,2-6 |
| Challenger Tenerife Qual | 2023/02/06 10:00 | Nicolas Alvarez Varona v Oscar Jose Gutierrez | 3-6,3-6 |
| Challenger Ottignies | 2023/01/23 09:00 | Oscar Jose Gutierrez v Henri Squire | 6-4,4-6,3-6 |