He remained undefeated in singles actions until finally losing to Ivan Koloff on a house show at the Omni in Atlanta on February 14, 1988. Simmons was dominant through the first half of the year against lower-level competition on house shows, including Whatley and The Terminator. Simmons teamed with Steve Williams at the 3rd Annual Jim Crockett Sr. Memorial Cup in Greenville, South Carolina on April 22, 1988. They were defeated in the opening round by Mike Rotunda and Kevin Sullivan when Simmons was hit with a foreign object. In December, he finally entered the first sustained losing streak of his career as he dropped multiple house show matches to Mike Rotunda.