2. Mr. McMahon – 1 (1999)
The 1999 Royal Rumble match was massively centered around the rivalry between Mr. McMahon and Steve Austin. The bitter rivals kicked things off with Austin entering as the number one entrant, and McMahon entered second. However, Austin and McMahon spent a large chunk of the Rumble outside of the ring as the Corporation attacked Austin backstage. When the coast was clear, McMahon undertook commentary duties.
McMahon had nowhere to run and nowhere to hide when Austin returned from the hospital, and pummeled McMahon from the broadcast table and into the ring. Furthermore, Austin looked poised to win a record-breaking third Rumble in succession, but that failed to materialize.
The new WWE Champion, The Rock, distracted Austin, allowing McMahon to sneak up from behind and eliminate Austin to become the winner of the 1999 Royal Rumble.
