Stadium: Central Round: 25 Ground: Hardcourt outdoor
| ITF Portugal F22 | 2018/10/27 15:00 | Cacao, Tiago v Monteiro, Joao | 6-7,7-5,1-6 |
| ITF Portugal F18 | 2018/09/28 11:10 | Cacao, Tiago v Monteiro, Joao | 4-6,6-3,6-2 |
| ITF Portugal F8 | 2018/04/20 12:40 | Monteiro, Joao v Cacao, Tiago | 4-6,5-7 |
| ITF Portugal F5 | 2018/03/23 10:00 | Monteiro, Joao v Cacao, Tiago | 6-4,6-1 |
| ITF Portugal F8 | 2016/07/15 12:00 | Monteiro, Joao v Cacao, Tiago | 6-1,6-4 |
| ITF M15 Sintra | 2020/09/17 12:00 | Nicolas Alvarez Varona v Monteiro, Joao | 6-2,3-6,6-4 |
| ITF M15 Sintra | 2020/09/16 12:35 | Monteiro, Joao v Benjamin Lock | 6-1,4-6,6-3 |
| ITF M15 Sintra | 2020/09/10 10:20 | Monteiro, Joao v Ojeda Lara, Ricardo | 6-4,4-6,6-4 |
| ITF M15 Sintra | 2020/09/08 08:30 | Monteiro, Joao v Fermin Tenti | 6-3,6-7,6-2 |
| FPT Portugal Series | 2020/07/18 13:30 | Nuno Borges v Monteiro, Joao | 4-6,6-3,5-4 |
| FPT Portugal Series | 2020/07/17 12:00 | Monteiro, Joao v Gastao Elias | 6-2,6-5 |
| FPT Portugal Series | 2020/07/16 15:00 | Monteiro, Joao v Duarte Vale | 6-7,7-6,6-3 |
| FPT Portugal Series | 2020/07/10 16:00 | Frederico Ferreira Silva v Monteiro, Joao | 6-0,6-2 |
| ITF M15 Castelo Branco | 2020/09/25 10:20 | Cacao, Tiago v Nicolas Alvarez Varona | 1-6,4-6 |
| ITF M15 Castelo Branco | 2020/09/24 15:50 | Gonzalo Lama v Cacao, Tiago | 3-6,7-6,3-6 |
| ITF M15 Castelo Branco | 2020/09/23 10:00 | Cacao, Tiago v Pedro Araujo | 6-4,6-4 |
| ITF M15 Sintra | 2020/09/17 12:00 | Carlos Gimeno Valero v Cacao, Tiago | 6-3,6-2 |
| ITF M15 Sintra | 2020/09/16 08:30 | Cacao, Tiago v Wilson Leite | 6-3,7-6 |
| ITF M15 Sintra | 2020/09/09 08:30 | Cacao, Tiago v Benjamin Pietri | 3-6,2-6 |
| FPT Portugal Series | 2020/07/19 15:00 | Cacao, Tiago v Nuno Borges | 2-6,3-6 |
| FPT Portugal Series | 2020/07/18 15:00 | Frederico Ferreira Silva v Cacao, Tiago | 3-6,1-0 |