Here is a list of Outlaw's best fights. For a list of Outlaw's losses, refer to "Sidney Outlaw Losses".
On June 25, 2021 Sidney Outlaw faced off against Myles Jury in a lightweight bout at age 29. He was coming in with a record of 16-4 (9), and Jury was 32 years old and with a record of 19-5 (13). Outlaw stopped Myles Jury via submission.
On May 2, 2014 Sidney Outlaw faced off against Mike Bannon in a lightweight bout at age 22. He was coming in with a record of 3-0 (2). Outlaw won the fight via 3-round unanimous decision.
On November 14, 2019 Sidney Outlaw faced off against Roger Huerta in a lightweight bout at age 27. He was coming in with a record of 14-3 (8), and Huerta was 36 years old and with a record of 24-11-1 (17). Outlaw won the fight via 3-round unanimous decision.
On August 21, 2020 Sidney Outlaw faced off against Adam Piccolotti in a lightweight bout at age 28. He was coming in with a record of 15-4 (8), and Piccolotti was 31 years old and with a record of 12-3 (8). Outlaw won the fight via 3-round split decision.
On August 11, 2023 Sidney Outlaw faced off against Islam Mamedov in a lightweight bout at age 31. He was coming in with a record of 17-5 (9). Outlaw won the fight via 3-round unanimous decision.
On June 29, 2018 Sidney Outlaw faced off against Raush Manfio in a welterweight bout at age 26. He was coming in with a record of 10-3 (5), and Manfio was 26 years old and with a record of 11-2 (7). Outlaw won the fight via 3-round unanimous decision.
On February 24, 2017 Sidney Outlaw fought Taj Abdul-Hakim in a welterweight title fight for the ROC Championship title. Outlaw was 24 years old and with a record of 7-3 (4). Outlaw won the fight via 3-round unanimous decision and is crowned the new welterweight world champion.
On September 21, 2018 Sidney Outlaw met Krzysztof Kułak in a welterweight (ROC Championship) title defense fight. Outlaw was 26 years old and with a record of 11-3 (6). Outlaw stopped Krzysztof Kułak via 2nd-round submission and successfully defended his title.
On June 14, 2013 Sidney Outlaw faced off against Steve Simms in a lightweight bout at age 21. He was coming in with a record of 2-0 (2). Outlaw stopped Steve Simms via submission.
On February 2, 2013 Sidney Outlaw faced off against Mtume Goodrum in a lightweight bout at age 20. He was coming in with a record of 1-0 (1). Outlaw stopped Mtume Goodrum via TKO.
