1999 • 21 Episodes
January 31, 1999
1. Dolly Parton vs. Jennifer Lopez 2. Madonna vs. Michael Jackson 3. Mike Tyson vs. Evander Holyfield
February 4, 1999
1. Ice Cube vs. Ice-T 2. Robert DeNiro vs. Al Pacino 3. Backstreet Boys vs. Beastie Boys
February 11, 1999
1. Calista Flockhart vs. Lucy Lawless 2. Boy George vs. Don Johnson 3. Penn & Teller vs. Siegfried & Roy
February 18, 1999
1. Jennifer Aniston vs. Courteney Cox vs. Lisa Kudrow 2. Sean Connery vs. Roger Moore 3. Gandhi vs. Genghis Khan
February 25, 1999
1. Moses vs. Pharaoh 2. Larry King vs. Geraldo Rivera 3. Neve Campbell vs. Sarah Michelle Gellar
March 4, 1999
1. Paul Hogan vs. Mel Gibson 2. Antonio Banderas vs. Cheech Marin 3. Fabio vs. Bono vs. Yoko Ono
March 11, 1999
1. Kate Moss vs. Claudia Schiffer vs. Tyra Banks 2. William Shakespeare vs. Busta Rhymes 3. The Real World's: Puck vs. Jon vs. Tami vs. Jacinda
April 22, 1999
It features fights that are about the elements of movies. The fights are Martin Scorsese vs. Oliver Stone in Fight 1, Fight 2 is Groucho Marx vs. John Wayne, and the Main Event is Cameron Diaz vs. Meryl Streep.
May 6, 1999
1. Emeril Lagasse vs. The Two Fat Ladies 2. Matt Pinfield vs. Jesse Camp 3. Alex Trebek vs. Pat Sajak
July 1, 1999
1. Bill Clinton vs. Kenneth Starr 2. James Van Der Beek vs. Saddam Hussein 3. Abe Lincoln vs. George Washington
July 8, 1999
1. Charlie Sheen vs. Emilio Estevez 2. Eric & Julia Roberts vs. Donny & Marie Osmond 3. Bob & Jakob Dylan vs. Jerry & Ben Stiller
July 15, 1999
1. Tommy Lee vs. Ron Jeremy 2. Alanis Morissette vs. Jewel 3. The Three Stooges vs. The Three Tenors
July 22, 1999
It's comedian time! 1. Dennis Miller vs. Carrot Top 2. Rodney Dangerfield vs. Don Rickles Main Event: Billy Crystal vs. Robin Williams vs. Whoopi Goldberg
July 29, 1999
1. Elton John vs. Ozzy Osbourne 2. Martha Stewart vs. Sandra Bernhard Main Event: Tom Hanks vs. Sean Penn
August 5, 1999
1. Ricky Schroder vs. Gary Coleman 2. Lauryn Hill vs. Shania Twain 3. Hugh Grant vs. All-comers [ Clint Eastwood, Harvey Keitel, & Andy Dick ]
October 7, 1999
1. Dennis Franz vs. Sammo Hung 2. Steven Wright vs. Chris Tucker 3. Gwyneth Paltrow vs. Winona Ryder
October 14, 1999
1. Cher vs. Bette Midler 2. Benito Mussolini vs. Roberto Benigni 3. John Travolta vs. Nicolas Cage
October 21, 1999
In this episode, the deathmatch cast interviews people in New York, about which fights they want to see.
October 28, 1999
1. Frankenstein's Monster vs. The Wolfman 2. Captain Doody vs. The Undertaker 3. 'N Sync vs. Kiss
November 4, 1999
1. Richard Simmons vs. Billy Blanks 2. Don King vs. Donald Trump 3. Brad Pitt vs. Keanu Reeves
November 11, 1999
1. Ben Affleck vs. Matt Damon 2. Ozzy Osbourne vs. Rob Zombie 3. Marilyn Manson vs. Ricky Martin