Round: 54 Ground: Hardcourt outdoor
| ITF M25 Claremont | 2019/10/09 20:05 | Errol Smith v Zane Khan | 4-6,7-6,3-6 |
| ITF M25 Edwardsville | 2019/08/07 17:25 | Ezekiel Clark v Errol Smith | 6-4,7-6 |
| ITF M25 Edwardsville | 2019/08/06 15:45 | Errol Smith v A.trice Pickens | 6-4,4-6,10-8 |
| ITF M25 Decatur | 2019/07/31 22:00 | Jenson Brooksby v Errol Smith | 6-3,6-2 |
| ITF M25 Champaign | 2019/07/25 19:45 | Oliver Crawford v Errol Smith | 4-6,6-1,6-1 |
| ITF M25 Champaign | 2019/07/24 17:00 | Errol Smith v Kyle Seelig | 7-6,6-4 |
| ITF M25 Iowa City | 2019/07/19 16:15 | Axel Geller v Errol Smith | 2-6,6-3,6-0 |
| ITF M25 Iowa City | 2019/07/18 14:00 | Errol Smith v Alejandro Gonzalez | 7-6,6-4 |
| ITF M25 Fayetteville | 2019/10/21 15:00 | John Mercer v Ian Chadwell | 6-4,6-4 |
| ITF M25 Claremont | 2019/10/07 18:00 | Piers Foley v Ian Chadwell | 6-7,6-4,10-8 |
| ITF M25 Claremont | 2019/10/06 18:00 | Anas Abdelouahid v Ian Chadwell | 3-6,2-6 |
| ITF M25 Decatur | 2019/07/29 18:00 | Eric Morris v Ian Chadwell | 6-1,6-2 |
| ITF M25 Iowa City | 2019/07/16 15:00 | Alexander Brown v Ian Chadwell | 6-4,3-6,13-11 |
| ITF M25 Iowa City | 2019/07/15 15:00 | Ian Chadwell v Korey Lovett | 6-0,6-2 |
| ITF M15 Norman | 2019/07/10 15:45 | Alexander Klintcharov v Ian Chadwell | 6-4,2-6,6-1 |
| ITF M15 Norman | 2019/07/08 14:00 | Ian Chadwell v Eric Morris | 6-0,6-2 |