Big Boss Man

Raymond "Ray" Walter Traylor, Jr. (May 2, 1963 – September 22, 2004) never won a Royal Rumble match, but had entered in the five matches. His highest place was in the 1999 Royal Rumble match where he came in 3rd place before being eliminated.

Match History
Boss Man entered the 1989 Royal Rumble match at #22 and eliminated Hulk Hogan with the help of his tag team partner Akeem before being eliminated by Hogan in response.

Boss Man also entered the 1992 Royal Rumble match at #13 and managed to eliminate Repo Man and Hercules by himself before being eliminated by Ric Flair.

Boss Man later entered the 1999 Royal Rumble match at #22 and eliminated X-Pac and D-Lo Brown by himself before being eliminated by Steve Austin.

Boss Man next entered the 2000 Royal Rumble match at #9 and managed to eliminate Chyna and Faarooq by himself and Rikishi with the help of Test, British Bulldog, Gangrel, Edge and Bob Backlund before being eliminated by The Rock.

Boss Man last entered the 2002 Royal Rumble match at #3 and did not eliminate anyone before being eliminated by Rikishi.