Oakman has also been a member of the Triangle Torch and the West Virginia Roughriders of the American Arena League (AAL), the Bismarck Bucks of Champions Indoor Football (CIF), the Los Angeles Wildcats of the XFL, the Wild Aces of Fan Controlled Football, and the Toronto Argonauts and Edmonton Elks of the CFL.

After the draft, he wasn't expected to get signed as an undrafted free agent due to the legal issues he was facing at the time.

[22] He helped lead the Triangle Torch to the AIF Championship but lost a close game to Cape Fear Heroes.

In June 2019, Shawn Oakman signed with the West Virginia Roughriders of the American Arena League.

[32] In 2022, he played and started in 17 regular season games and recorded 28 defensive tackles, six sacks, and one forced fumble, en route to a second CFL East All-Star award.

[31] He also played and started in the 109th Grey Cup where he had two defensive tackles and one sack as the Argonauts defeated the Winnipeg Blue Bombers and Oakman won his first championship.

[38] On February 25, 2012, Oakman was involved in an incident at a Penn State dining hall, and was eventually charged by PSU police with disorderly conduct, harassment, and retail theft.

[39] According to police, Oakman fled the scene after shoving a cashier who refused to return his student ID over unpaid items.

[39] In a later interview, Oakman stated that the cashier withheld his ID after she found that there were no points on his meal card and that he had only grabbed her wrist to retrieve it and return to his dorm room.

[4] According to Oakman, this incident led to his dismissal from the Penn State football team by then head coach Bill O'Brien.

[4] Oakman was named in a January 2013 Waco police incident report alleging he physically assaulted a woman.

According to the report, Oakman grabbed the alleged victim under her armpits and shoved her into brick walls and cabinets at her South Waco apartment.

The alleged incident was about six months after Oakman enrolled at Baylor after being kicked off the football team at Penn State University for physically assaulting a female cashier who reportedly tried to stop him from stealing food from a campus store.

[42] On July 20, 2016, a grand jury in McLennan County indicted Oakman on charges of second-degree felony sexual assault.