Stadium: Cancha 3 Round: 25 Ground: Hardcourt outdoor
| Challenger Oeiras Qual | 2021/04/04 15:10 | Nick Chappell v Henrique Rocha | 4-6,2-6 |
| Marbella, Spain | 2021/03/29 09:00 | Javier Barranco Cosano v Nick Chappell | 6-2,7-6 |
| Marbella, Spain | 2021/03/28 12:15 | Fermin Tenti v Nick Chappell | 0-6,0-6 |
| Challenger - Lugano | 2021/03/21 09:00 | Vitaliy Sachko v Nick Chappell | 6-3,6-1 |
| Challenger - Cleveland | 2021/03/16 19:10 | Nick Chappell v Smith, Roy | 4-6,7-5,4-6 |
| ITF - M25 Naples | 2021/02/24 14:50 | Hidalgo, Diego v Nick Chappell | 6-3,1-6,6-4 |
| Challenger Potchefstroom Qual | 2021/02/14 11:20 | Jack Draper v Nick Chappell | 6-4,6-4 |
| Challenger Potchefstroom | 2021/02/13 09:00 | Nick Chappell v Benjamin Bonzi | 1-6,2-6 |
| Challenger - Oeiras | 2021/04/05 12:30 | Carlos Gimeno Valero v Ortega-Olmedo, Roberto | 6-1,6-1 |
| Challenger - Oeiras | 2021/04/01 15:30 | Gastao Elias v Ortega-Olmedo, Roberto | 3-6,6-1,6-3 |
| Challenger - Oeiras | 2021/03/30 15:30 | Ortega-Olmedo, Roberto v Ernesto Escobedo | 7-5,6-4 |
| ITF - M25 La Nucia | 2021/03/17 10:45 | Bondarevskiy, Yan v Ortega-Olmedo, Roberto | 6-3,6-3 |
| Challenger St. Petersburg | 2021/03/11 08:00 | Mirza Basic v Ortega-Olmedo, Roberto | 6-1,7-6 |
| Challenger St. Petersburg | 2021/03/09 07:00 | Ortega-Olmedo, Roberto v Quiroz, Roberto | 6-3,6-3 |
| Challenger Gran Canaria | 2021/03/02 11:35 | Ortega-Olmedo, Roberto v Alex Molcan | 3-6,6-7 |
| Challenger Gran Canaria | 2021/02/25 13:20 | Ortega-Olmedo, Roberto v Andrea Pellegrino | 4-6,5-7 |