Level, 2 wins each over 4 singles meetings since 2023. Last meeting on 30/09/2026 at Curitiba Challenger.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 30/09/2026 | Curitiba Challenger | Round 1 | clay | Villanueva | 3-6 6-3 5-2 |
| 26/11/2025 | Temuco Challenger | Round 2 | hard | Angelo | 6-4 4-6 6-5 |
| 28/09/2023 | M25 Lujan | Round 2 | clay | Angelo | 6-2 6-4 |
| 22/08/2023 | Lima Challenger | Round 1 | clay | Villanueva | 6-3 1-6 7-5 |
| clay | Villanueva 2 - 1 Angelo |
| hard | Villanueva 0 - 1 Angelo |
| 2026 | Villanueva 1 - 0 Angelo |
| 2025 | Villanueva 0 - 1 Angelo |
| 2023 | Villanueva 1 - 1 Angelo |
224 wins, 191 losses since 2021 (54.0%).
Last matches: D D D D D
151 wins, 105 losses since 2021 (59.0%).
Last matches: D V D V D
Level, 2 wins each over 4 singles meetings since 2023.
On 30/09/2026, at Curitiba Challenger (Round 1): Gonzalo Villanueva won 3-6 6-3 5-2.