| # | Wrestler | Date | Place | Special Note |
| 1 | Jim Duggan | January 24, 1988 | Hamilton, Onatrio, Canada | 1 |
| 2 | Big John Studd | January 25, 1989 | Houston, Texas | 2 |
| 3 | Hulk Hogan | January 21, 1990 | Orlando, Florida | 3 |
| 4 | Hulk Hogan[2] | January 19, 1991 | Miami, Flrodia | 4 |
| 5 | Ric Flair | January 19, 1992 | Albany, New York | 5 |
| 6 | Yokozuna | January 23, 1993 | Sacramento, California | 6 |
| 7 | Bret Hart & Lex Luger | January 22, 1994 | Providence, Rhode Island | 7 |
| 8 | Shawn Michaels | January 22, 1995 | Tampa, Florida | 8 |
| 9 | Shawn Michaels[2] | January 21, 1996 | Fresno, California | 9 |
| 10 | Steve Austin | January 19, 1997 | San Antonio, Texas | 10 |
| 11 | Steve Austin[2] | January 18, 1998 | San Jose, California | 11 |
| 12 | Vince McMahon | January 24, 1999 | San Jose, California | 12 |
| 13 | The Rock | January 23, 2000 | New York City, New York | 13 |
| 14 | Steve Austin[3] | January 21, 2001 | New Orleans, Louisiana | 14 |
| 15 | Hunter Hearst Helmsley | January 20, 2002 | Atlanta, Georgia | 15 |
| 16 | Brock Lesnar | January 19, 2003 | Boston, Massachusetts | 16 |
| 17 | Chris Benoit | January 25, 2004 | Philadelphia, Pennsylvania | 17 |
| 18 | Batista | January 30, 2005 | Fresno, California | 18 |
| 19 | Rey Mysterio | January 29, 2006 | Miami, Florida | 19 |
| 20 | The Undertaker | January 28, 2007 | San Antonio, Texas | 20 |
Notes:
1. Eliminated One Man Gang to win. 20 man battle royal(the rest became 30 man battle royals)
2. Eliminated Ted Dibiase to win
3. Eliminated Mr Perfect(Curt Hennig) to win
4. Elimiated Earthquake to win and become first man to win it twice and to win it twice consecuativly
5. Eliminated Sid to win the rumble and the WWF Title
6. Eliminated Randy Savage to win
7. Hart & Luger elmiated each other simultaneouly and were both declared the winner
8. Eliminated "British Bulldog" Davey Boy Smith to win & was #1 entry.
9. Eliminated Diesel(Kevin Nash) to win & become second person to win it twice and consectuativly
10. Eliminated Bret Hart to win
11. Elimiated Rocky Mavia(The Rock) to win and be the third to win it twice and consecuativly
12. Eliminated Steve Austin to win
13. Elimiated Big Show to win
14. Eliminated Kane to win and be the first to win it three times
15. Eliminated Kurt Angle to win
16. Eliminated The Undertaker to win
17. Eliminated The Big Show to win & was #1 entry.
18. Eliminated John Cena to win.
19. Eliminated Randy Orton to win.
20. Eliminated Shawn Michaels to win and is now the first person to win the Rumble as the 30th entry.
