Tyron Woodley has three losses against two opponents on his boxing record. For a list of Woodley's best fights, refer to "Best fights of Tyron Woodley".
On December 19, 2025 Tyron Woodley faced off against Anderson Silva at age 43. He was coming in with a record of 0-3 (0), and Silva was 50 years old and with a record of 3-2 (2). Woodley lost the fight via 2nd-round TKO.
On December 18, 2021 Tyron Woodley faced off against Jake Paul at age 39. He was coming in with a record of 0-2 (0), and Paul was 24 years old and with a record of 4-0 (3). Woodley lost the fight via 6th-round KO.
On August 29, 2021 Tyron Woodley faced off against Jake Paul at age 39. He was coming in with a record of 0-1 (0), and Paul was 24 years old and with a record of 3-0 (3). Woodley lost the fight via 8-round split decision.
