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