Continuing his pursuit of the WWE Championship, Kozlov competed in and was unsuccessful in winning a Beat the Clock Challenge match against ECW Champion Matt Hardy for another title shot. This led to the two meeting at Armageddon, where Kozlov gained his first pay-per-view win by defeating Hardy in a non-title match. Kozlov competed in the 2009 Royal Rumble match, entering as the sixth participant, but was eliminated by Triple H after eliminating The Great Khali, Carlito, and Montel Vontavious Porter. He then qualified to be part of the No Way Out Elimination Chamber match, where he was pinned for the first time after receiving a Last Ride from The Undertaker, though he still remained unpinned in one-on-one competition. Kozlov's undefeated streak in televised singles competition ended on the March 2, 2009 episode of "Raw", in which he was defeated by Shawn Michaels; this match was for the opportunity to face The Undertaker at WrestleMania XXV. His first televised singles loss on "SmackDown" came against The Undertaker himself on March 13.