Stadium: Stadium 4 Round: 25 Ground: Hardcourt outdoor
| US Open Qual | 2016/08/26 18:10 | Jared Donaldson v Santiago Giraldo | 6-2,6-2 |
| Challenger Columbus | 2019/01/10 16:00 | Santiago Giraldo v Scott Griekspoor | 1-6,4-6 |
| Challenger Columbus | 2019/01/09 16:00 | Santiago Giraldo v Evan King | 6-4,6-4 |
| Challenger Guayaquil | 2018/11/03 01:00 | Guido Andreozzi v Santiago Giraldo | 6-4,7-6 |
| Challenger Guayaquil | 2018/11/02 01:10 | Juan Ignacio Londero v Santiago Giraldo | 7-5,6-7,6-7 |
| Challenger Guayaquil | 2018/10/31 16:00 | Santiago Giraldo v Miljan Zekic | 7-5,7-5 |
| Challenger Guayaquil | 2018/10/29 19:15 | Santiago Giraldo v Joao Domingues | 7-5,6-3 |
| Challenger Lima | 2018/10/22 20:20 | Thiago Monteiro v Santiago Giraldo | 1-6,6-2,7-5 |
| Challenger Santo Domingo | 2018/10/11 14:00 | Santiago Giraldo v Carlos Berlocq | 6-7,6-7 |
| ATP Toronto | 2018/08/06 15:00 | Jared Donaldson v Benoit Paire | 3-6,4-6 |
| ATP Washington | 2018/08/01 20:30 | Stefanos Tsitsipas v Jared Donaldson | 3-6,6-3,7-5 |
| ATP Washington | 2018/07/31 20:20 | Jared Donaldson v Jordan Thompson | 6-4,7-6 |
| Wimbledon | 2018/07/04 15:10 | Stefanos Tsitsipas v Jared Donaldson | 6-3,6-2,3-6,4-6,6-3 |
| Wimbledon | 2018/07/02 15:15 | Malek Jaziri v Jared Donaldson | 6-7,3-6,1-6 |
| ATP Eastbourne | 2018/06/27 10:00 | Jared Donaldson v Denis Shapovalov | 4-6,6-4,2-6 |
| ATP Eastbourne | 2018/06/25 10:00 | Jared Donaldson v Taylor Fritz | 6-7,6-3,7-6 |
| ATP Queens | 2018/06/18 13:20 | Jared Donaldson v Frances Tiafoe | 4-6,6-7 |