| 2021 Charlottesville Men's Pro Challenger | |
|---|---|
| Date | 1–7 November |
| Edition | 12th |
| Surface | Hard (indoor) |
| Location | Charlottesville, United States |
| Champions | |
| Singles | |
 Stefan Kozlov | |
| Doubles | |
| William Blumberg / Max Schnur | |
The 2021 Jonathan Fried Pro Challenger was a professional tennis tournament played on indoor hardcourts. It was the twelfth edition of the tournament which was part of the 2021 ATP Challenger Tour, taking place in Charlottesville, United States from November 1 to 7, 2021.
| Country | Player | Rank1 | Seed |
|---|---|---|---|
 CAN | Vasek Pospisil | 85 | 1 |
 JPN | Taro Daniel | 120 | 2 |
| USA | Mitchell Krueger | 147 | 3 |
| USA | Jack Sock | 152 | 4 |
 KAZ | Dmitry Popko | 162 | 5 |
 TPE | Jason Jung | 166 | 6 |
| USA | Bjorn Fratangelo | 172 | 7 |
 SLO | Blaž Rola | 177 | 8 |
The following players received wildcards into the singles main draw:
Martin Damm Emilio Nava 
Jeffrey von der SchulenburgThe following player received entry into the singles main draw using a protected ranking:
The following players received entry into the singles main draw as alternates:
The following players received entry from the qualifying draw:
Stefan Kozlov def. 
Aleksandar Vukic 6–2, 6–3. William Blumberg / Max Schnur def. 
Treat Huey / 
Frederik Nielsen 3–6, 6–1, [14–12].