| 2013-02-04 | Vina del Mar | Clay | R32 | 101 |  Albert Montanes | 578 |  Nicolas Massu (WC) | 6-7(6) 6-3 6-4 | H2H | 3 | 179 | 8 | 4 | 63.4% | 68.8% | 56.8% | 4/6 |
| 2012-01-30 | Vina del Mar | Clay | R32 | 172 |  Federico Delbonis (Q) | 503 | Nicolas Massu (WC) | 6-0 6-3 | H2H | 3 | 77 | 1 | 2 | 75.7% | 82.1% | 66.7% | 0/0 |
| 2011-09-16 | Davis Cup WG PO: CHI vs ITA | Hard | RR | 923 |  Daniele Bracciali | 446 | Nicolas Massu | 4-3 RET | H2H | 5 | - | - | - | - | - | - | - |
| 2011-03-04 | Davis Cup WG R1: CHI vs USA | Clay | RR | 8 |  Andy Roddick | 241 | Nicolas Massu | 6-2 4-6 6-3 6-4 | H2H | 5 | - | - | - | - | - | - | - |
| 2011-01-31 | Santiago | Clay | R32 | 316 |  Caio Zampieri (Q) | 210 | Nicolas Massu (WC) | 7-6(7) 7-5 | H2H | 3 | 158 | 5 | 2 | 60.2% | 72.0% | 48.5% | 5/7 |
| 2010-07-09 | Davis Cup WG QF: CHI vs CZE | Clay | RR | 247 |  Ivo Minar | 101 | Nicolas Massu | 6-0 6-2 6-3 | H2H | 5 | - | - | - | - | - | - | - |
| 2010-06-21 | Wimbledon | Grass | R128 | 152 |  Ilija Bozoljac (Q) | 99 | Nicolas Massu | 7-6(3) 3-6 6-3 7-6(7) | H2H | 5 | 180 | 27 | 2 | 66.4% | 84.0% | 51.2% | 2/4 |
| 2010-05-24 | Roland Garros | Clay | R128 | 92 | Fabio Fognini | 91 | Nicolas Massu | 6-1 3-6 2-6 6-3 6-3 | H2H | 5 | 214 | 5 | 7 | 63.6% | 72.0% | 40.4% | 4/9 |
| 2010-05-03 | Estoril | Clay | R32 | 114 |  Rui Machado (WC) | 92 | Nicolas Massu | 6-2 6-4 | H2H | 3 | 91 | 2 | 2 | 73.0% | 67.4% | 58.8% | 5/6 |
| 2010-04-05 | Houston | Clay | R32 | 94 | Nicolas Massu | 86 |  Mischa Zverev | 6-4 6-2 | H2H | 3 | 90 | 3 | 4 | 69.1% | 68.4% | 58.8% | 5/7 |
