Shelton Benjamin made his wrestling debut in July 1999 in the prestigious Ohio Valley Wrestling gym, where he formed a tag team with Brock Lesnar, already his partner at the University of Minnesota; the two captured the Southern Tag Team Championships three times.

Following Lesnar's promotion to the main roster in March 2002, Benjamin teamed up with Redd Dogg Begnaud, with whom he captured the tag team titles for the fourth time. In the meantime he wrestles in several house shows in dark matches and in some television tapings of WWE's Sunday Night Heat as a face.

Shelton makes his roster debut on the SmackDown! and with Charlie Haas, like him a former All American, he joined Kurt Angle's Team Angle.

The two will win the pair titles twice. The first time against Los Guerreros, a tag team formed by Eddie and Chavo Guerrero Jr., the second time against Eddie Guerrero and Tajiri, the latter replacing Chavo.

After a long absence due to injury, he returned to singles competition on Raw on November 7, being defeated by Austin Theory. After several one-time appearances, he re-teamed with Cedric Alexander and on the January 9 episode of Raw, the two engaged in a tag team turmoil match to determine the contenders for The Usos' Raw Tag Team Championship but were eliminated by Damian Priest and Finn Bálor. On the March 31 episode of SmackDown, he entered the annual André the Giant Memorial Battle Royal but was eliminated.

On May 1, 2023, as a result of the Draft, he became a free agent. On the May 15 episode of Raw, Benjamin participated in a battle royal to determine Gunther's challenger for the Intercontinental Championship but was eliminated by the Viking Raiders.