1. Deathbowl '99

0

. 31 January 1999

1. Dolly Parton vs. Jennifer Lopez 2. Madonna vs. Michael Jackson 3. Mike Tyson vs. Evander Holyfield

2. The Battle of Boys With Toys

0

. 4 February 1999

1. Ice Cube vs. Ice-T 2. Robert DeNiro vs. Al Pacino 3. Backstreet Boys vs. Beastie Boys

3. Magic, Flashbacks and Pregnancies

0

. 11 February 1999

1. Calista Flockhart vs. Lucy Lawless 2. Boy George vs. Don Johnson 3. Penn & Teller vs. Siegfried & Roy

4. The Time Machine

0

. 18 February 1999

1. Jennifer Aniston vs. Courteney Cox vs. Lisa Kudrow 2. Sean Connery vs. Roger Moore 3. Gandhi vs. Genghis Khan

5. The Unknown Murderer

0

. 25 February 1999

1. Moses vs. Pharaoh 2. Larry King vs. Geraldo Rivera 3. Neve Campbell vs. Sarah Michelle Gellar

6. Celebrity Deathmatch Internacional

0

. 4 March 1999

1. Paul Hogan vs. Mel Gibson 2. Antonio Banderas vs. Cheech Marin 3. Fabio vs. Bono vs. Yoko Ono

7. The End of the Real World

0

. 11 March 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

8. Celebrity Deathmatch - The Motion Picture

0

. 22 April 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.

9. Cable Day

0

. 6 May 1999

1. Emeril Lagasse vs. The Two Fat Ladies 2. Matt Pinfield vs. Jesse Camp 3. Alex Trebek vs. Pat Sajak

10. 4th of July Celebration

0

. 1 July 1999

1. Bill Clinton vs. Kenneth Starr 2. James Van Der Beek vs. Saddam Hussein 3. Abe Lincoln vs. George Washington

11. Family Night I

0

. 8 July 1999

1. Charlie Sheen vs. Emilio Estevez 2. Eric & Julia Roberts vs. Donny & Marie Osmond 3. Bob & Jakob Dylan vs. Jerry & Ben Stiller

12. Censoring Problems

0

. 15 July 1999

1. Tommy Lee vs. Ron Jeremy 2. Alanis Morissette vs. Jewel 3. The Three Stooges vs. The Three Tenors

13. Salute to Laughter

0

. 22 July 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

14. The Laser Pointer

0

. 29 July 1999

1. Elton John vs. Ozzy Osbourne 2. Martha Stewart vs. Sandra Bernhard Main Event: Tom Hanks vs. Sean Penn

15. Robot Nicky

0

. 5 August 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 ]

16. The Prophecy

0

. 7 October 1999

1. Dennis Franz vs. Sammo Hung 2. Steven Wright vs. Chris Tucker 3. Gwyneth Paltrow vs. Winona Ryder

17. In The Memory Of Stacy Cornbred

0

. 14 October 1999

1. Cher vs. Bette Midler 2. Benito Mussolini vs. Roberto Benigni 3. John Travolta vs. Nicolas Cage

18. From The Streets Of New York

0

. 21 October 1999

In this episode, the deathmatch cast interviews people in New York, about which fights they want to see.

19. Halloween Episode I

0

. 28 October 1999

1. Frankenstein's Monster vs. The Wolfman 2. Captain Doody vs. The Undertaker 3. 'N Sync vs. Kiss

20. High Tech Fighting

0

. 4 November 1999

1. Richard Simmons vs. Billy Blanks 2. Don King vs. Donald Trump 3. Brad Pitt vs. Keanu Reeves

21. Fandemonium II

0

. 11 November 1999

1. Ben Affleck vs. Matt Damon 2. Ozzy Osbourne vs. Rob Zombie 3. Marilyn Manson vs. Ricky Martin