Estádio: Court 1 Round: 28 Ground: Hardcourt outdoor
| ITF - M25 Idanha-a-Nova | 2021/07/23 09:00 | Anton Matusevich v Gilbert S K Junior | 3-6,3-6 |
| ITF - M25 Idanha-a-Nova | 2021/07/22 08:00 | Gilbert S K Junior v Roy Smith | 6-3,6-2 |
| ITF - M25 Idanha-a-Nova | 2021/07/21 09:50 | Garrett Johns v Gilbert S K Junior | 5-7,1-6 |
| ITF - M15 Saraievo | 2021/06/03 09:00 | Gilbert S K Junior v Matheus P De Almeida | 6-4,3-6,3-6 |
| ITF - M15 Saraievo | 2021/06/02 09:00 | Gilbert S K Junior v Kristjan Tamm | 6-4,6-2 |
| ITF - M25 Kiseljak | 2021/05/26 15:30 | Gilbert S K Junior v David Pichler | 4-6,3-6 |
| ITF - M15 Brcko | 2021/05/21 09:00 | Gilbert S K Junior v Eric Vanshelboim | 6-2,4-6,0-6 |
| ITF - M15 Prijedor | 2021/05/11 12:35 | Luca Giacomini v Gilbert S K Junior | 6-3,1-6,6-1 |
| ITF - M25 Idanha-a-Nova | 2021/07/23 09:00 | Simon Carr v Alafia Ayeni | 6-2,6-4 |
| ITF - M25 Idanha-a-Nova | 2021/07/22 08:00 | Sho Shimabukuro v Simon Carr | 6-7,6-4,2-6 |
| ITF - M25 Idanha-a-Nova | 2021/07/20 11:15 | Simon Carr v Duarte Vale | 6-4,7-6 |
| ITF - M25 Idanha-a-Nova | 2021/07/16 10:00 | Simon Carr v Anton Matusevich | 4-6,6-4,4-6 |
| ITF - M25 Idanha-a-Nova | 2021/07/15 10:45 | Simon Carr v Alejandro Moro Canas | 4-6,6-3,6-4 |
| ITF - M25 Idanha-a-Nova | 2021/07/13 12:05 | Antoine Bellier v Simon Carr | 4-6,5-7 |
| ITF - M15 Almada | 2021/07/07 10:20 | Terence Das v Simon Carr | 3-6,1-6 |
| Taça Davis | 2021/06/19 09:35 | Aleksandre Metreveli v Simon Carr | 2-6,2-6 |