| US Open | 08/23 15:00 | 45 | [120] Peter Polansky v Santiago Giraldo [337] | 7-6,6-4 | |
| US Open | 08/21 21:45 | 44 | [337] Santiago Giraldo v Viktor Galovic [225] | 6-4,6-4 | |
| Challenger Vancouver | 08/14 01:40 | 25 | [123] Peter Polansky v Santiago Giraldo [327] | 7-6,5-7,6-3 | |
| ATP Gstaad Qual | 07/21 10:50 | 64 | [139] Adrian M-Maceiras v Santiago Giraldo [285] | 6-3,7-5 | |
| ATP Bastad Qual | 07/15 08:30 | 64 | [142] Henri Laaksonen v Santiago Giraldo [286] | 4-6,6-2,6-4 | |
| Challenger Bastad | 07/09 09:00 | 25 | [286] Santiago Giraldo v Thiago Monteiro [130] | Cancelled | |
| Wimbledon Qual | 06/25 10:55 | 44 | [220] Brayden Schnur v Santiago Giraldo [281] | 6-4,7-5 | |
| French Open | 05/30 10:30 | 24 | Roberto Bautista-Agut v Santiago Giraldo | 6-4,7-5,6-3 | |
| French Open | 05/28 12:15 | 23 | [84] Marcos Baghdatis v Santiago Giraldo [315] | Retired | |
| French Open Qual | 05/25 10:25 | 46 | [312] Santiago Giraldo v Simone Bolelli [130] | 6-0,6-2 | |
| French Open Qual | 05/24 08:00 | 45 | [312] Santiago Giraldo v Uladzimir Ignatik [203] | 6-7,6-2,6-2 | |
| French Open Qual | 05/21 13:00 | 44 | [150] Adrian Menendez-Maceiras v Santiago Giraldo [312] | 2-6,4-6 | |
| Challenger Puerto Vallarta | 05/03 23:00 | 27 | [310] Santiago Giraldo v Carlos Gomez-Herrera [298] | 6-1,5-7,6-7 | |
| Challenger Puerto Vallarta | 05/02 23:45 | 26 | [247] Alexander Sarkissian v Santiago Giraldo [310] | 3-6,6-7 | |
| Challenger Puerto Vallarta | 05/01 00:45 | 25 | Marcelo Sepulveda v Santiago Giraldo | 2-6,0-6 | |
| Challenger Guadalajara | 04/18 02:00 | 25 | [293] Santiago Giraldo v Jose H-Fernandez [263] | Retired | |
| Challenger Mexico City | 04/10 17:00 | 25 | [291] Santiago Giraldo v Mats Moraing [156] | 4-6,7-5,2-6 | |
| Davis Cup | 04/08 01:40 | 28 | Santiago Giraldo v Guilherme Clezar | Cancelled | |
| Davis Cup | 04/06 20:00 | 28 | [290] Santiago Giraldo v Thiago Monteiro [125] | 1-6,2-6 | |
| Challenger Le Gosier | 03/27 19:30 | 25 | [288] Santiago Giraldo v Ante Pavic [302] | 2-6,6-3,6-7 | |
| ATP Miami Qual | 03/19 19:10 | 44 | [288] Santiago Giraldo v Elias Ymer [133] | 6-7,4-6 | |
| Davis Cup | 09/17 15:00 | 26 | [131] Santiago Giraldo v Marin Cilic [5] | 3-6,4-6,4-6 | |
| Davis Cup | 09/15 17:10 | 26 | [131] Santiago Giraldo v Franko Skugor [324] | 6-4,4-6,5-7,6-4,6-2 | |
| US Open | 08/31 21:20 | 24 | [37] Philipp Kohlschreiber v Santiago Giraldo [129] | Retired | |
| US Open | 08/30 19:45 | 23 | [164] Vincent Millot v Santiago Giraldo [129] | 1-6,0-6,6-4,6-4,4-6 | |
| Challenger Santo Domingo | 08/16 20:00 | 26 | [333] Evan King v Santiago Giraldo [131] | Retired | |
| Challenger Santo Domingo | 08/16 02:15 | 25 | Nick Hardt v Santiago Giraldo | 1-6,0-6 | |
| ATP Kitzbuhel | 08/02 16:00 | 26 | [150] Gerald Melzer v Santiago Giraldo [122] | 6-3,7-6 | |
| ATP Kitzbuhel | 08/01 09:00 | 25 | [122] Santiago Giraldo v Robin Haase [52] | 7-6,4-6,6-4 | |
| ATP Kitzbuhel Qual | 07/30 09:30 | 46 | [99] Santiago Giraldo v Jozef Kovalik [150] | 7-5,6-4 |