He played college football for the Toledo Rockets and was selected by the Bengals in the seventh round of the 2018 NFL draft.

He was also previously a member of the Tennessee Titans and Atlanta Falcons, as well as the San Antonio Commanders of the Alliance of American Football (AAF).

[4][5] On November 28, Woodside recorded a career-high five touchdowns against Eastern Michigan and Toledo ending the season as co-MAC West champs.

[6] He ranked fourth in passing efficiency and completion percentage in the MAC, leading the Rockets to a win over Arkansas State in the GoDaddy Bowl.

[12] He was named MAC West Division Player and Male Scholar Athlete of the Week for his performance.

[15][16] On November 9, Woodside scored three touchdowns in the 28-point comeback win against Northern Illinois, outscoring the Huskies 28–10 in the second half.

[25] On November 24, he recorded 300 yards and two touchdowns in a 37–10 win over Western Michigan, claiming the West Division crown.

[26] In the Mid-American Conference Championship game against Akron, Woodside recorded 307 yards and four touchdowns in a 45–28 win.

[28] Woodside was named First-team All-MAC, MAC Offensive Player of the Year, and received the Vern Smith Leadership Award.

[29] Woodside led the team to a 10–2 record, giving the Toledo Rockets their first participation in the MAC Football Championship since 2004.

[39] In Week 5 of the 2019 AAF season against the Arizona Hotshots, Woodside completed 21 of 27 passes for 290 yards, two touchdowns, one interception, and a 120.7 passer rating en route to a San Antonio 29–25 win.