| Singles | |
|---|---|
| 2020 Cary Challenger | |
| Champion |  Denis Kudla |
| Runner-up |  Prajnesh Gunneswaran |
| Score | 3–6, 6–3, 6–0 |
Andreas Seppi was the defending champion [1] but chose not to defend his title.
Denis Kudla won the title after defeating Prajnesh Gunneswaran 3–6, 6–3, 6–0 in the final.
Thiago Monteiro (second round) Denis Kudla (champion)
Daniel Elahi Galán (semifinals) Prajnesh Gunneswaran (final)
Mohamed Safwat (first round) Michael Mmoh (second round, withdrew)
Dmitry Popko (quarterfinals) Mackenzie McDonald (first round)| Semifinals | Final | ||||||||||||
 Mikael Torpegaard | |||||||||||||
| 4 | Prajnesh Gunneswaran | w/o | |||||||||||
| 4 | Prajnesh Gunneswaran | 6 | 3 | 0 | |||||||||
| 2 | Denis Kudla | 3 | 6 | 6 | |||||||||
| 3 | Daniel Elahi Galán | 78 | 1 | 4 | |||||||||
| 2 | Denis Kudla | 66 | 6 | 6 | |||||||||
| First round | Second round | Quarterfinals | Semifinals | ||||||||||||||||||||||||
| 1 | T Monteiro | 77 | 3 | ||||||||||||||||||||||||
| G Clezar | 65 | 2r | 1 | T Monteiro | 6 | 3 | 4 | ||||||||||||||||||||
| M Torpegaard | 3 | 6 | 6 | M Torpegaard | 4 | 6 | 6 | ||||||||||||||||||||
| WC | W Blumberg | 6 | 3 | 4 | M Torpegaard | 6 | 3 | 7 | |||||||||||||||||||
| T-S Kwiatkowski | 6 | 4 | 5 | B Nakashima | 2 | 6 | 5 | ||||||||||||||||||||
| B Nakashima | 4 | 6 | 7 | B Nakashima | 6 | 6 | |||||||||||||||||||||
| WC |  A Galarneau | 6 | 4 | 6 | WC | A Galarneau | 3 | 2 | |||||||||||||||||||
| 8 | M McDonald | 2 | 6 | 1 | M Torpegaard | ||||||||||||||||||||||
| 4 | P Gunneswaran | 6 | 6 | 4 | P Gunneswaran | w/o | |||||||||||||||||||||
| P Polansky | 2 | 2 | 4 | P Gunneswaran | 63 | 6 | 77 | ||||||||||||||||||||
| B Fratangelo | 611 | 3 | J Sock | 77 | 2 | 65 | |||||||||||||||||||||
| J Sock | 713 | 6 | 4 | P Gunneswaran | 3 | 7 | 77 | ||||||||||||||||||||
| R Ramanathan | 6 | 4 | 1 | Q | T Bellucci | 6 | 5 | 65 | |||||||||||||||||||
 T Gabashvili | 3 | 6 | 6 | T Gabashvili | 3 | 67 | |||||||||||||||||||||
| Q | T Bellucci | 64 | 6 | 79 | Q | T Bellucci | 6 | 79 | |||||||||||||||||||
| 5 | M Safwat | 77 | 1 | 67 | |||||||||||||||||||||||
| First round | Second round | Quarterfinals | Semifinals | ||||||||||||||||||||||||
| 6 | M Mmoh | 7 | 6 | ||||||||||||||||||||||||
| Q | A Nedovyesov | 5 | 0 | 6 | M Mmoh | ||||||||||||||||||||||
| C Eubanks | 7 | 7 | C Eubanks | w/o | |||||||||||||||||||||||
| Q | C Harrison | 5 | 5 | C Eubanks | 4 | 4 | |||||||||||||||||||||
 H Moriya | 65 | 1 | 3 | DE Galán | 6 | 6 | |||||||||||||||||||||
 T-l Wu | 77 | 6 | T-l Wu | 3 | 3 | ||||||||||||||||||||||
 R Cid Subervi | 65 | 1 | 3 | DE Galán | 6 | 6 | |||||||||||||||||||||
| 3 | DE Galán | 77 | 6 | 3 | DE Galán | 78 | 1 | 4 | |||||||||||||||||||
| 7 | D Popko | 6 | 6 | 2 | D Kudla | 66 | 6 | 6 | |||||||||||||||||||
| U Blanch | 3 | 2 | 7 | D Popko | 6 | 3 | 6 | ||||||||||||||||||||
 E Ymer | 1 | 2 | M Krueger | 3 | 6 | 3 | |||||||||||||||||||||
| M Krueger | 6 | 6 | 7 | D Popko | 4 | 1 | |||||||||||||||||||||
| N Rubin | 6 | 3 | 5 | 2 | D Kudla | 6 | 6 | ||||||||||||||||||||
| WC | Garrett Johns | 4 | 6 | 7 | WC | G Johns | 2 | 1 | |||||||||||||||||||
| Q | K King | 2 | 1 | 2 | D Kudla | 6 | 6 | ||||||||||||||||||||
| 2 | D Kudla | 6 | 6 | ||||||||||||||||||||||||
Juan Martín del Potro was the defending champion and successfully defended his title, defeating Roger Federer in the final, 7–6(7–3), 2–6, 6–4.
Lucas Pouille was the defending champion, but lost in the semifinals to Milos Raonic.
John Isner was the defending champion, but withdrew before the tournament began.
John Isner was the defending champion and successfully defended his title, defeating Ryan Harrison in a rematch of the 2017 final, 5–7, 6–3, 6–4.
Sam Querrey was the defending champion, but lost in the second round to Egor Gerasimov.
Denis Istomin was the defending champion, but chose not to participate this year.
Yuki Bhambri was the defending champion but chose not to defend his title.
Prajnesh Gunneswaran was the defending champion but lost in the final to Jay Clarke.
Robert Galloway and Denis Kudla were the defending champions but chose not to defend their title.
Alexander Zverev was the two-time defending champion, but lost to Cristian Garín in the quarterfinals.
Roger Federer was the defending champion, but chose not to participate this year.
Thomas Fabbiano was the defending champion but chose not to defend his title.
Dominic Thiem was the defending champion and chose not to defend his title, as he was still competing at the 2020 US Open.
Marcos Giron was the defending champion but chose not to defend his title.
Brandon Nakashima was the defending champion but chose not to defend his title.
Emilio Gómez was the defending champion but chose not to defend his title.
Denis Kudla was the defending champion but chose not to defend his title.
Aslan Karatsev defeated Andy Murray in the final, 6–3, 6–3 to win the men's singles title at the 2022 Sydney Tennis Classic. This was Murray's first ATP final since he won the 2019 European Open.
Adrian Mannarino was the defending champion but chose not to defend his title.
Stefan Kozlov was the defending champion but lost in the first round to Prajnesh Gunneswaran.