Stadium: Cancha 8 Round: 14 Ground: Clay
| Challenger Puerto Vallarta | 2021/11/23 05:25 | Alejandro Tabilo v Adrian Menendez-Maceiras | 6-3,6-2 |
| ATP Stockholm | 2021/11/07 13:00 | Adrian Menendez-Maceiras v Viktor Durasovic | 3-6,2-6 |
| ATP Stockholm | 2021/11/06 16:25 | Mohamed Safwat v Adrian Menendez-Maceiras | 4-6,6-7 |
| Challenger Alicante | 2021/10/12 10:15 | Oscar Otte v Adrian Menendez-Maceiras | 6-2,6-3 |
| ATP Indian Wells | 2021/10/05 20:55 | Evgeny Donskoy v Adrian Menendez-Maceiras | 6-7,7-6,7-5 |
| Challenger Lima | 2021/09/28 15:00 | Johan Nikles v Adrian Menendez-Maceiras | 6-4,6-2 |
| Challenger Ambato | 2021/09/21 16:30 | Adrian Menendez-Maceiras v Nerman Fatic | 2-6,5-7 |
| Challenger Quito | 2021/09/16 15:00 | Adrian Menendez-Maceiras v Thiago Agustin Tirante | 5-7,2-6 |
| Challenger Champaign | 2021/11/17 17:25 | Stefan Kozlov v Keegan Smith | 6-3,6-1 |
| Challenger Champaign | 2021/11/15 16:00 | Keegan Smith v Tristan Boyer | 7-6,6-3 |
| Challenger Champaign | 2021/11/14 17:10 | Michael Redlicki v Keegan Smith | 3-6,7-6,3-6 |
| ITF M15 Fayetteville | 2021/11/06 15:00 | Keegan Smith v Alfredo Perez | 6-4,1-6,2-6 |
| ITF M15 Fayetteville | 2021/11/05 15:00 | Daniel Rodrigues v Keegan Smith | 7-6,1-6,2-6 |
| ITF M15 Fayetteville | 2021/11/04 18:05 | Gabi Adrian Boitan v Keegan Smith | 5-7,2-6 |
| ITF M15 Fayetteville | 2021/11/03 18:35 | Francisco Rocha v Keegan Smith | 6-4,4-6,4-6 |
| ITF M25 Calabasas | 2021/10/26 22:45 | Omni Kumar v Keegan Smith | 6-7,6-4,6-2 |