| Feb 14, 2026 | Dominguez | 1–0 | Caballero | Round 3: Dominguez, Facundo - Caballero, Tabare | French Defense: Rubinstein Variation, Blackburne Defense | |
| Feb 13, 2026 | Cayetano | ½–½ | Caballero | Round 1: Cayetano, Juan - Caballero, Tabare | French Defense: Exchange Variation | |
| Feb 1, 2026 | Estrada Nieto | 1–0 | Caballero | Round 3: Estrada Nieto, Julian - Caballero, Tabare | French Defense: Rubinstein Variation, Blackburne Defense | |
| Dec 10, 2025 | Nandwani Narwani | 1–0 | Caballero | Round 8: Nandwani Narwani, Suraj Sriram - Caballero, Tabare | Bogo-Indian Defense: Exchange Variation | |
| Dec 10, 2025 | Caballero | ½–½ | Sepulveda Brango | Round 7: Caballero, Tabare - Sepulveda Brango, Alberto Enrique | Sicilian Defense: Closed, Botvinnik Defense, with f4 | |
| Dec 8, 2025 | Coaquira Gonzales | 1–0 | Caballero | Round 4: Coaquira Gonzales, Oscar Adriano - Caballero, Tabare | French Defense: Advance Variation, Milner-Barry Gambit, Hector Variation | |
| Dec 6, 2025 | Herrera Jimenez | 1–0 | Caballero | Round 2: Herrera Jimenez, Mateo - Caballero, Tabare | Nimzo-Indian Defense: Sämisch Variation | |
| Apr 22, 2024 | Olmos | 0–1 | Caballero | Round 5: Olmos, Ciro - Caballero, Tabare | French Defense: Exchange Variation | |
| Apr 21, 2024 | Caballero | ½–½ | Cardarelli | Round 4: Caballero, Tabare - Cardarelli, Leon | Pirc Defense: Byrne Variation | |
| Apr 21, 2024 | Costa | 0–1 | Caballero | Round 3: Costa, Milagros - Caballero, Tabare | French Defense: Exchange Variation | |
| Apr 20, 2024 | Caballero | 1–0 | Diaz | Round 2: Caballero, Tabare - Diaz, Alan | Italian Game: Hungarian Defense | |
| Apr 20, 2024 | Lamas | 0–1 | Caballero | Round 1: Lamas, Joaquin - Caballero, Tabare | French Defense: Advance Variation, Paulsen Attack | |
| Aug 1, 2021 | Caballero | 1–0 | Renji | World Youth Cup 2021 O10-G18 - Open 10 | Sicilian Defense: Closed, Traditional | |
| Aug 1, 2021 | Caballero | ½–½ | Salimu | World Youth Cup 2021 O10-G18 - Open 10 | Scandinavian Defense: Modern Variation | |
| Aug 1, 2021 | Caballero | 1–0 | Luo | World Youth Cup 2021 O10-G18 - Open 10 | Italian Game: Deutz Gambit | |
| Aug 1, 2021 | Caballero | 0–1 | Aaroh Mutyalapati | World Youth Cup 2021 O10-G18 - Open 10 | Sicilian Defense: Closed | |
| Aug 1, 2021 | Das | 1–0 | Caballero | World Youth Cup 2021 O10-G18 - Open 10 | French Defense: Exchange Variation | |
| Aug 1, 2021 | Nguyen | 1–0 | Caballero | World Youth Cup 2021 O10-G18 - Open 10 | Nimzo-Indian Defense | |
| Aug 1, 2021 | Wimalarathne | 1–0 | Caballero | World Youth Cup 2021 O10-G18 - Open 10 | French Defense: Exchange Variation | |
| Aug 1, 2021 | Federer | 1–0 | Caballero | World Youth Cup 2021 O10-G18 - Open 10 | Catalan Opening: Closed | |
