| ATP - Houston | 04/12 01:35 | 26 | [224] Giraldo, Santiago v Jordan Thompson [67] | 6-4,6-7,5-7 | |
| ATP - Houston | 04/09 20:55 | 25 | [224] Giraldo, Santiago v Klahn, Bradley [93] | 6-4,6-4 | |
| ATP - Houston | 04/07 15:00 | 164 | [150] Christopher Eubanks v Giraldo, Santiago [230] | 4-6,4-6 | |
| ATP - Houston | 04/06 19:00 | 64 | [230] Giraldo, Santiago v Ward, James [180] | 6-4,6-4 | |
| Monterrey, Mexico | 04/04 23:05 | 26 | [217] Young, Donald v Giraldo, Santiago [230] | 6-3,6-4 | |
| Monterrey, Mexico | 04/03 19:20 | 25 | [230] Giraldo, Santiago v Quiroz, Roberto [176] | 3-6,7-5,7-6 | |
| Monterrey, Mexico | 04/01 22:50 | 24 | [282] Roberto Cid Subervi v Giraldo, Santiago [230] | 6-7,3-6 | |
| Challenger - Indian Wells | 02/28 19:50 | 26 | [105] Daniel Evans v Giraldo, Santiago [243] | 6-1,6-2 | |
| Challenger - Indian Wells | 02/27 20:20 | 25 | [243] Giraldo, Santiago v Donaldson, Jared [129] | 6-2,2-6,6-4 | |
| Challenger - Indian Wells | 02/25 23:30 | 24 | [243] Giraldo, Santiago v Novikov, Dennis [359] | 7-5,5-7,6-2 | |
| Challenger - Morelos | 02/21 19:10 | 26 | [248] Giraldo, Santiago v Steven Diez [311] | 6-3,1-6,1-6 | |
| Challenger - Morelos | 02/20 02:00 | 25 | [248] Giraldo, Santiago v Redlicki, Michael [351] | 6-4,7-5 | |
| Coupe Davis | 02/02 20:20 | - | Giraldo, Santiago v Ymer, Mikael | Cancelled | |
| Coupe Davis | 02/01 21:00 | - | [251] Giraldo, Santiago v Elias Ymer [116] | 6-2,6-4 | |
| Newport Beach, USA | 01/22 19:20 | 25 | [120] Jason Jung v Giraldo, Santiago [253] | 7-6,7-6 | |
| Newport Beach, USA | 01/21 20:30 | 24 | [253] Giraldo, Santiago v Marcora, Roberto [286] | 6-3,7-6 | |
| Challenger Columbus | 01/10 16:00 | 26 | [254] Giraldo, Santiago v Griekspoor, Scott [288] | 1-6,4-6 | |
| Challenger Columbus | 01/09 16:00 | 25 | [254] Giraldo, Santiago v King, Evan [304] | 6-4,6-4 | |
| Challenger Guayaquil | 11/03 01:00 | 28 | [97] Guido Andreozzi v Giraldo, Santiago [312] | 6-4,7-6 | |
| Challenger Guayaquil | 11/02 01:10 | 27 | [119] Londero, Juan Ignacio v Giraldo, Santiago [312] | 7-5,6-7,6-7 | |
| Challenger Guayaquil | 10/31 16:00 | 26 | [312] Giraldo, Santiago v Zekic, Miljan [267] | 7-5,7-5 | |
| Challenger Guayaquil | 10/29 19:15 | 25 | [312] Giraldo, Santiago v Joao Domingues [222] | 7-5,6-3 | |
| Challenger Lima | 10/22 20:20 | 25 | [115] Thiago Monteiro v Giraldo, Santiago [310] | 1-6,6-2,7-5 | |
| Santo Domingo, Dominican Republic | 10/11 14:00 | 26 | [326] Giraldo, Santiago v Berlocq, Carlos [138] | 6-7,6-7 | |
| Santo Domingo, Dominican Republic | 10/10 02:20 | 25 | [65] Cuevas, Pablo v Giraldo, Santiago [326] | 6-7,6-2,3-6 | |
| Monterrey, Mexico | 10/06 19:00 | 28 | [137] Karlovic, Ivo v Giraldo, Santiago [412] | 6-7,6-4,7-6 | |
| Monterrey, Mexico | 10/05 20:00 | 27 | [152] Gerald Melzer v Giraldo, Santiago [412] | 7-6,5-7,3-6 | |
| Monterrey, Mexico | 10/03 22:20 | 26 | [412] Giraldo, Santiago v Escobar, Gonzalo [441] | 4-6,6-2,6-4 | |
| Monterrey, Mexico | 10/02 18:00 | 25 | Krainik, Pavel v Giraldo, Santiago | 4-6,4-6 | |
| Coupe Davis | 09/14 14:00 | 26 | [14] Diego Schwartzman v Giraldo, Santiago [410] | 6-3,6-1,6-7,6-1 |