| Kitzbühel, Autriche, Qualifications | 07/29 09:00 | 45 | [99] Giraldo, Santiago v Hampel, Lenny [371] | 6-1,6-2 | |
| Gstaad, Switzerland | 07/25 08:00 | 25 | [99] Giraldo, Santiago v Joao Sousa [61] | 3-6,3-6 | |
| Challenger San Benedetto | 07/19 19:30 | 26 | [97] Giraldo, Santiago v Matteo Berrettini [229] | Retired | |
| Challenger San Benedetto | 07/17 19:30 | 25 | Giraldo, Santiago v Marcora, Roberto | 1-6,6-3,6-2 | |
| Challenger Perugia | 07/13 16:00 | 26 | [101] Giraldo, Santiago v Stefanos Tsitsipas [192] | 4-6,5-7 | |
| Challenger Perugia | 07/11 11:20 | 25 | [101] Giraldo, Santiago v Kenny de Schepper [151] | 7-6,6-4 | |
| Wimbledon Qual | 06/26 13:35 | 44 | [99] Giraldo, Santiago v Stefanos Tsitsipas [190] | 6-2,4-6,3-6 | |
| Challenger Poprad Tatry | 06/21 09:00 | 26 | [224] Sebastian Ofner v Giraldo, Santiago [100] | 4-6,6-4,7-6 | |
| Challenger Poprad Tatry | 06/19 10:20 | 25 | [216] Bellotti, Riccardo v Giraldo, Santiago [100] | 5-7,6-3,1-6 | |
| Lisbon, Portugal | 06/13 14:25 | 25 | [99] Giraldo, Santiago v Balazs, Attila [205] | 3-6,3-6 | |
| French Open, Paris, France | 05/29 12:20 | 23 | [107] Giraldo, Santiago v Seppi, Andreas [83] | 6-4,1-6,2-6,2-6 | |
| French Open Qual | 05/25 14:15 | 46 | [107] Giraldo, Santiago v Guido Andreozzi [123] | 6-3,6-2 | |
| French Open Qual | 05/24 08:00 | 45 | [107] Giraldo, Santiago v Ignatik, Uladzimir [149] | 6-2,6-4 | |
| French Open Qual | 05/22 10:45 | 44 | [107] Giraldo, Santiago v Zemlja, Grega [219] | 6-1,6-4 | |
| ATP Rome Qual | 05/13 11:00 | 45 | [68] Berlocq, Carlos v Giraldo, Santiago [111] | 6-2,6-1 | |
| ATP Madrid Qual | 05/07 09:00 | 46 | [47] Adrian Mannarino v Giraldo, Santiago [100] | 6-4,7-6 | |
| ATP Madrid Qual | 05/06 09:00 | 45 | [100] Giraldo, Santiago v Thiago Monteiro [81] | 6-4,5-7,7-6 | |
| ATP - Barcelone | 04/25 17:35 | 24 | [99] Giraldo, Santiago v Zeballos, Horacio [84] | 2-6,3-6 | |
| ATP Barcelona Qual | 04/23 10:45 | 46 | Giraldo, Santiago v Davidovich Fokina, Alejandro | 5-7,6-3,6-2 | |
| ATP Barcelona Qual | 04/22 08:00 | 45 | [102] Giraldo, Santiago v Lopez Perez [184] | 2-6,7-6,6-3 | |
| Coupe Davis | 04/09 15:00 | 28 | [105] Giraldo, Santiago v Garin, Cristian [192] | 6-7,6-3,6-3,6-7,6-3 | |
| Coupe Davis | 04/07 15:00 | 28 | [105] Giraldo, Santiago v Nicolas Jarry [193] | 4-6,6-2,6-2,7-6 | |
| Miami, USA, Qualifying | 03/20 19:30 | 44 | [105] Giraldo, Santiago v Smyczek, Tim [166] | 4-6,3-6 | |
| Irving, USA | 03/15 17:00 | 25 | [150] Becker, Benjamin v Giraldo, Santiago [103] | 7-5,6-2 | |
| ATP - Indian Wells | 03/11 01:30 | 23 | [103] Giraldo, Santiago v Jan-Lennard Struff [63] | 3-6,4-6 | |
| Indian Wells, USA, Qualifying | 03/08 20:30 | 45 | [103] Giraldo, Santiago v Norbert Gombos [114] | 7-5,3-6,6-2 | |
| Indian Wells, USA, Qualifying | 03/07 22:05 | 44 | [103] Giraldo, Santiago v Michael Mmoh [185] | 6-3,7-6 | |
| Acapulco, Mexico, Qualifying | 02/26 03:15 | 26 | Radu Albot v Giraldo, Santiago | 5-7,6-0,6-2 | |
| ATP - Delray Beach | 02/21 17:20 | 25 | Giraldo, Santiago v Borna Coric | 2-6,3-6 | |
| Quito, Ecuador | 02/08 19:15 | 26 | Giraldo, Santiago v Renzo Olivo | 6-7,6-2,3-6 |