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