| 1996-11-04 | Santiago | Clay | R32 | 156 |  Alejandro Hernandez | 250 |  Sergio Cortes (WC) | 6-3 3-6 6-2 | H2H | 3 | 102 | 12 | 3 | 50.0% | 85.0% | 47.5% | 6/8 |
| 1996-02-09 | Davis Cup G1 QF: CHI vs BRA | Clay | RR | 225 |  Jaime Oncins | 231 | Sergio Cortes | 6-3 6-4 7-5 | H2H | 5 | - | - | - | - | - | - | - |
| 1996-02-09 | Davis Cup G1 QF: CHI vs BRA | Clay | RR | 70 | Fernando Meligeni | 231 | Sergio Cortes | 6-1 6-1 7-5 | H2H | 5 | - | - | - | - | - | - | - |
| 1995-09-11 | Bogota | Clay | R16 | 281 |  Miguel Tobon (WC) | 236 | Sergio Cortes (Q) | 7-5 7-5 | H2H | 3 | 90 | 4 | 3 | 54.9% | 61.5% | 56.3% | 5/9 |
| 1995-09-11 | Bogota | Clay | R32 | 236 | Sergio Cortes (Q) | 305 | Mario Rincon (WC) | 6-3 6-0 | H2H | 3 | 58 | 1 | 1 | 56.1% | 78.3% | 66.7% | 1/1 |
| 1995-07-31 | Prague | Clay | R16 | 560 |  Mariano Zabaleta (Q) | 230 | Sergio Cortes | 6-4 6-4 | H2H | 3 | 93 | 2 | 1 | 62.7% | 48.6% | 40.9% | 2/7 |
| 1995-07-31 | Prague | Clay | R32 | 230 | Sergio Cortes | 69 |  Jaime Yzaga (8) | 4-6 7-6(6) 6-3 | H2H | 3 | 133 | 1 | 2 | 49.5% | 63.5% | 45.3% | 9/15 |
| 1994-10-24 | Santiago | Clay | R32 | 61 |  Marcelo Filippini | 164 | Sergio Cortes (WC) | 6-3 1-6 7-6(0) | H2H | 3 | 138 | 2 | 2 | 59.6% | 71.4% | 50.0% | 4/8 |
| 1994-09-12 | Bogota | Clay | R16 | 144 | Sergio Cortes | 40 |  Andrei Chesnokov (3) | 7-5 6-7(7) 6-3 | H2H | 3 | 120 | 6 | 4 | 50.5% | 63.0% | 46.7% | 5/11 |
| 1994-09-12 | Bogota | Clay | R32 | 144 | Sergio Cortes | 227 |  Peter Tramacchi | 6-4 6-3 | H2H | 3 | 71 | 0 | 0 | 67.2% | 70.7% | 50.0% | 4/5 |
