| Coupe Davis | 03/07 21:40 | 45 | Giraldo, Santiago v Mayer, Leonardo | Cancelled | |
| Coupe Davis | 03/06 22:25 | 45 | [292] Giraldo, Santiago v Londero, Juan Ignacio [62] | 7-6,3-6,2-6 | |
| Challenger - Morelos | 02/21 01:40 | 26 | [442] Aziz Dougaz v Giraldo, Santiago [276] | 7-5,6-4 | |
| Challenger - Morelos | 02/19 21:30 | 25 | Manuel Sanchez v Giraldo, Santiago | 5-7,4-6 | |
| Bangkok-2, Thailand | 01/21 05:45 | 25 | [170] Istomin, Denis v Giraldo, Santiago [277] | 6-3,7-6 | |
| Bangkok-2, Thailand | 01/20 06:10 | 24 | [277] Giraldo, Santiago v Goncalo Oliveira [273] | Retired | |
| Bangkok, Thaïlande | 01/15 04:50 | 26 | [306] Arnaboldi, Andrea v Giraldo, Santiago [278] | 4-6,7-6,6-4 | |
| Bangkok, Thaïlande | 01/14 03:00 | 25 | [497] Sidharth Rawat v Giraldo, Santiago [278] | 6-3,6-7,4-6 | |
| Coupe Davis | 11/18 15:00 | 1 | [158] Darcis, Steve v Giraldo, Santiago [277] | 6-3,6-2 | |
| Challenger Cassis | 09/05 12:25 | 26 | [232] Giraldo, Santiago v Dmitry Popko [236] | Retired | |
| Challenger Cassis | 09/04 15:00 | 25 | [103] Jaziri, Malek v Giraldo, Santiago [232] | Retired | |
| Challenger Cassis | 09/02 08:30 | 24 | Giraldo, Santiago v Cabos, Vivien | 6-4,6-2 | |
| US Open, New York, USA | 08/27 15:00 | 23 | [75] Alexander Bublik v Giraldo, Santiago [232] | 2-6,6-0,7-5,3-6,6-4 | |
| US Open, New York, USA | 08/23 15:00 | 46 | [218] Mirza Basic v Giraldo, Santiago [231] | 6-7,4-6 | |
| US Open, New York, USA | 08/21 19:50 | 45 | [231] Giraldo, Santiago v Zverev, Mischa [292] | 7-5,6-3 | |
| US Open, New York, USA | 08/19 20:45 | 44 | [180] Marcora, Roberto v Giraldo, Santiago [231] | 4-6,3-6 | |
| Challenger San Benedetto | 07/18 12:55 | 26 | [236] Giraldo, Santiago v Arnaboldi, Andrea [219] | 6-4,3-6,6-7 | |
| Challenger San Benedetto | 07/16 14:50 | 25 | [236] Giraldo, Santiago v Varillas, Juan Pablo [338] | 6-4,6-2 | |
| Challenger Perugia | 07/08 12:25 | 24 | [252] Tristan Lamasine v Giraldo, Santiago [240] | 7-5,6-7,7-6 | |
| Ludwigshafen, Allemagne | 07/03 12:45 | 25 | [240] Giraldo, Santiago v Stefano Travaglia [102] | 1-6,6-7 | |
| Ludwigshafen, Allemagne | 07/02 09:00 | 24 | [289] Benjamin Bonzi v Giraldo, Santiago [240] | Retired | |
| Wimbledon, London, Great Britain | 06/24 12:40 | 44 | [243] Giraldo, Santiago v Oscar Otte [153] | 3-6,5-7 | |
| Challenger Almaty | 06/06 06:00 | 26 | [211] Giraldo, Santiago v Lorenzo Giustino [159] | 1-6,3-6 | |
| Challenger Almaty | 06/04 09:40 | 25 | [211] Giraldo, Santiago v Tung-Lin Wu [272] | 2-6,6-3,6-2 | |
| French Open, Paris, France | 05/23 14:30 | 46 | [177] Rudolf Molleker v Giraldo, Santiago [213] | 4-6,6-4,6-4 | |
| French Open, Paris, France | 05/22 10:40 | 45 | [213] Giraldo, Santiago v Gianluca Mager [143] | Retired | |
| French Open, Paris, France | 05/20 12:45 | 44 | [193] Nedovyesov, Aleksandr v Giraldo, Santiago [213] | 6-3,4-6,3-6 | |
| Challenger - Tallahassee | 04/23 18:10 | 25 | [202] Giraldo, Santiago v Sumit Nagal [344] | Retired | |
| Challenger - Sarasota | 04/17 15:35 | 25 | [119] Laaksonen, Henri v Giraldo, Santiago [206] | 6-4,6-4 | |
| Challenger - Sarasota | 04/16 15:40 | 24 | [206] Giraldo, Santiago v Thai-Son Kwiatkowski [259] | 5-7,6-1,6-4 |