| # | Name | Release date | Timing |
|---|---|---|---|
| 1 | Deathbowl '99 1. Dolly Parton vs. Jennifer Lopez 2. Madonna vs. Michael Jackson 3. Mike Tyson vs. Evander Holyfield |
1999-01-31 | — |
| 2 | The Battle of Boys With Toys 1. Ice Cube vs. Ice-T 2. Robert DeNiro vs. Al Pacino 3. Backstreet Boys vs. Beastie Boys |
1999-02-04 | — |
| 3 | Magic, Flashbacks and Pregnancies 1. Calista Flockhart vs. Lucy Lawless 2. Boy George vs. Don Johnson 3. Penn & Teller vs. Siegfried & Roy |
1999-02-11 | — |
| 4 | The Time Machine 1. Jennifer Aniston vs. Courteney Cox vs. Lisa Kudrow 2. Sean Connery vs. Roger Moore 3. Gandhi vs. Genghis Khan |
1999-02-18 | — |
| 5 | The Unknown Murderer 1. Moses vs. Pharaoh 2. Larry King vs. Geraldo Rivera 3. Neve Campbell vs. Sarah Michelle Gellar |
1999-02-25 | — |
| 6 | Celebrity Deathmatch Internacional 1. Paul Hogan vs. Mel Gibson 2. Antonio Banderas vs. Cheech Marin 3. Fabio vs. Bono vs. Yoko Ono |
1999-03-04 | — |
| 7 | The End of the Real World 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 |
1999-03-11 | — |
| 8 | Celebrity Deathmatch - The Motion Picture 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. |
1999-04-22 | — |
| 9 | Cable Day 1. Emeril Lagasse vs. The Two Fat Ladies 2. Matt Pinfield vs. Jesse Camp 3. Alex Trebek vs. Pat Sajak |
1999-05-06 | — |
| 10 | 4th of July Celebration 1. Bill Clinton vs. Kenneth Starr 2. James Van Der Beek vs. Saddam Hussein 3. Abe Lincoln vs. George Washington |
1999-07-01 | — |
| 11 | Family Night I 1. Charlie Sheen vs. Emilio Estevez 2. Eric & Julia Roberts vs. Donny & Marie Osmond 3. Bob & Jakob Dylan vs. Jerry & Ben Stiller |
1999-07-08 | — |
| 12 | Censoring Problems 1. Tommy Lee vs. Ron Jeremy 2. Alanis Morissette vs. Jewel 3. The Three Stooges vs. The Three Tenors |
1999-07-15 | — |
| 13 | Salute to Laughter 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 |
1999-07-22 | — |
| 14 | The Laser Pointer 1. Elton John vs. Ozzy Osbourne 2. Martha Stewart vs. Sandra Bernhard Main Event: Tom Hanks vs. Sean Penn |
1999-07-29 | — |
| 15 | Robot Nicky 1. Ricky Schroder vs. Gary Coleman 2. Lauryn Hill vs. Shania Twain 3. Hugh Grant vs. All-comers [ Clint Eastwood, Harvey Keitel, & Andy Dick ] |
1999-08-05 | — |
| 16 | The Prophecy 1. Dennis Franz vs. Sammo Hung 2. Steven Wright vs. Chris Tucker 3. Gwyneth Paltrow vs. Winona Ryder |
1999-10-07 | — |
| 17 | In The Memory Of Stacy Cornbred 1. Cher vs. Bette Midler 2. Benito Mussolini vs. Roberto Benigni 3. John Travolta vs. Nicolas Cage |
1999-10-14 | — |
| 18 | From The Streets Of New York In this episode, the deathmatch cast interviews people in New York, about which fights they want to see. |
1999-10-21 | — |
| 19 | Halloween Episode I 1. Frankenstein's Monster vs. The Wolfman 2. Captain Doody vs. The Undertaker 3. 'N Sync vs. Kiss |
1999-10-28 | — |
| 20 | High Tech Fighting 1. Richard Simmons vs. Billy Blanks 2. Don King vs. Donald Trump 3. Brad Pitt vs. Keanu Reeves |
1999-11-04 | — |
| 21 | Fandemonium II 1. Ben Affleck vs. Matt Damon 2. Ozzy Osbourne vs. Rob Zombie 3. Marilyn Manson vs. Ricky Martin |
1999-11-11 | — |
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