# 2021 Charlottesville Men's Pro Challenger – Singles

Vasek Pospisil was the defending champion but lost in the first round to Emilio Nava.
Stefan Kozlov won the title after defeating Aleksandar Vukic 6–2, 6–3 in the final.

## Seeds

* Vasek Pospisil (first round)
* Taro Daniel (first round)
* Mitchell Krueger (first round)
* Jack Sock (quarterfinals)
* Dmitry Popko (first round)
* Jason Jung (first round)
* Bjorn Fratangelo (first round)
* Blaž Rola (first round)

## Draw
### Key

* Q = Qualifier
* WC = Wild card
* LL = Lucky loser
* Alt = Alternate
* SE = Special exempt
* PR = Protected ranking
* ITF = ITF entry
* JE = Junior exempt
* w/o = Walkover
* r = Retired
* d = Defaulted
* SR = Special ranking

### Finals

| Semifinals | Semifinals | Semifinals | Semifinals | Semifinals | Final | Final | Final | Final |
| Alt | Stefan Kozlov | 6 | 6$^1$ | 6 | | | | |
| | J. J. Wolf | 1 | 7$^7$ | 0 | | | | |
| | J. J. Wolf | 1 | 7$^7$ | 0 | Alt | Stefan Kozlov | 6 | 6 |
| | | | | | | Aleksandar Vukic | 2 | 3 |
| | Aleksandar Vukic | 6 | 6 | | | Aleksandar Vukic | 2 | 3 |
| | Brayden Schnur | 4 | 1 | | | | | |

### Top half

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals | Semifinals | Semifinals |
| 1 | V Pospisil | 4 | 6 | 6$^3$ | | | | | | | | | | | | | | |
| WC | Em Nava | 6 | 4 | 7$^7$ | WC | Em Nava | 2 | 7$^7$ | 6 | | | | | | | | | |
| | T Ito | 6$^0$ | 5 | | Alt | G Soeda | 6 | 6$^5$ | 2 | | | | | | | | | |
| Alt | G Soeda | 7$^7$ | 7 | | | | | | | WC | Em Nava | 4 | 2 | | | | | |
| WC | Jeffrey von der Schulenburg | 6$^5$ | 5 | | | | | | | Alt | S Kozlov | 6 | 6 | | | | | |
| | J Kubler | 7$^7$ | 7 | | | J Kubler | 3 | 1 | | | | | | | | | | |
| Alt | S Kozlov | 7 | 6 | | Alt | S Kozlov | 6 | 6 | | | | | | | | | | |
| 7 | B Fratangelo | 5 | 2 | | | | | | | | | | | Alt | S Kozlov | 6 | 6$^1$ | 6 |
| 3 | M Krueger | 3 | 2 | | | | | | | | | | | | J. J. Wolf | 1 | 7$^7$ | 0 |
| Q | D Kudla | 6 | 6 | | Q | D Kudla | 2 | 6$^5$ | | | | | | | | | | |
| | J. J. Wolf | 7 | 6 | | | J. J. Wolf | 6 | 7$^7$ | | | | | | | | | | |
| WC | M Damm | 5 | 4 | | | | | | | | J. J. Wolf | 7 | 6 | | | | | |
| Alt | Yo Watanuki | 6 | 2 | 6 | | | | | | | T-S Kwiatkowski | 5 | 4 | | | | | |
| | C Eubanks | 2 | 6 | 4 | Alt | Yo Watanuki | 6$^4$ | 1 | | | | | | | | | | |
| | T-S Kwiatkowski | 7$^7$ | 2 | 7 | | T-S Kwiatkowski | 7$^7$ | 6 | | | | | | | | | | |
| 8 | B Rola | 6$^3$ | 6 | 5 | | | | | | | | | | | | | | |

### Bottom half

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals |
| 5 | D Popko | 3 | 5 | | | | | | | | | | | | | |
| | A Vukic | 6 | 7 | | | A Vukic | 3 | 6 | 6 | | | | | | | |
| Q | N Chappell | 4 | 3 | | Alt | T-l Wu | 6 | 3 | 2 | | | | | | | |
| Alt | T-l Wu | 6 | 6 | | | | | | | | A Vukic | 6 | 7 | | | |
| | C-M Stebe | 6 | 6$^1$ | 6 | | | | | | 4 | J Sock | 4 | 5 | | | |
| | M Mmoh | 4 | 7$^7$ | 2 | | C-M Stebe | 2 | 3 | | | | | | | | |
| | M Torpegaard | 4 | 4 | | 4 | J Sock | 6 | 6 | | | | | | | | |
| 4 | J Sock | 6 | 6 | | | | | | | | | | | A Vukic | 6 | 6 |
| 6 | J Jung | 5 | 4 | | | | | | | | | | | B Schnur | 4 | 1 |
| Q | C Harrison | 7 | 6 | | Q | C Harrison | 6$^1$ | 7$^7$ | 6$^6$ | | | | | | | |
| | Y Uchiyama | 6 | 2 | 0 | | B Schnur | 7$^7$ | 6$^4$ | 7$^8$ | | | | | | | |
| | B Schnur | 2 | 6 | 6 | | | | | | | B Schnur | 7 | 6 | | | |
| Q | I Montes de la Torre | 6 | 4 | 7$^7$ | | | | | | | P Gunneswaran | 5 | 3 | | | |
| PR | P Polansky | 3 | 6 | 6$^5$ | Q | I Montes de la Torre | 1 | 5 | | | | | | | | |
| | P Gunneswaran | 6$^2$ | 7$^7$ | 6 | | P Gunneswaran | 6 | 7 | | | | | | | | |
| 2 | T Daniel | 7$^7$ | 6$^5$ | 2 | | | | | | | | | | | | |