At the Royal Rumble pay-per-view on January 27, 2019, Benjamin competed in the Royal Rumble match, but was eliminated by Braun Strowman. On the March 11 episode of "Raw", Benjamin surprisingly appeared and attacked Seth Rollins, and later faced Rollins in a losing effort. In the following months, Benjamin would be mostly off WWE programming, only wrestling in two battle royals: the André the Giant Memorial Battle Royal at WrestleMania 35 in April, and the 51-man battle royal at Super ShowDown in June; he would win neither match however. In August, Benjamin was announced as one of sixteen competitors in the King of the Ring, where he was defeated by his former tag team partner Chad Gable in the first round on the August 27 episode of "SmackDown Live". As part of the 2019 draft, Benjamin was drafted to the Raw brand. On January 26, 2020, Benjamin participated in the Royal Rumble match and entered at #10 at the namesake pay-per-view, but was eliminated by the WWE Champion Brock Lesnar.