List of Royal Rumble 1999 Match Results

The Rock def. Mankind — WWF Championship — I Quit Match — Main Event

Rock Won Title — Repeated Chair Shots Controversy — I Quit Tape Played

The Rock (with Corporation) defeated Mankind in a controversial I Quit Match to retain the WWF Championship — Rock delivered repeated unprotected chair shots to the handcuffed Mankind, and played a pre-recorded tape of Mankind saying 'I quit' from an interview. The match is still discussed for its extreme violence.

Vince McMahon won the 30-Man Royal Rumble — Entry #2 — Last Eliminated Steve Austin

Mr. McMahon Won — Austin Had $100,000 Bounty on His Head — Vince Eliminated Austin Last

Vince McMahon (entering at #2) won the Royal Rumble match by last eliminating Steve Austin — McMahon had placed a $100,000 bounty on Austin's head to recruit competitors to eliminate him. The Corporation members flooded the ring to protect Vince. The match also featured the Corporate Rumble pre-show where Chyna won the #30 entry for Vince. Vince McMahon is the only non-wrestler owner/promoter to win the Royal Rumble.