Henry Wingo spent time as a youth playing for Northwest Nationals and Crossfire FC.

[4] Wingo made his professional debut on March 4, coming on as a substitute during the first game of the 2017 season in a 2–1 loss to Houston.

[5] On August 12, 2019, Wingo moved to Norwegian Eliteserien side Molde FK, reuniting him with former Sounder Magnus Wolff Eikrem.

[12][13] On 20 April 2024, the Ferencváros–Kisvárda tie ended with a goalless draw at the Groupama Aréna on the 29th match day of the 2023–24 Nemzeti Bajnokság I season[14] which meant that Ferencváros won their 35th championship.

[19] After leaving Ferencváros, Wingo subsequently signed with Major League Soccer side Toronto FC on July 18, 2024.