Air date: 1999-01-31

Runtime: min

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

Air date: 1999-02-04

Runtime: min

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

Air date: 1999-02-11

Runtime: min

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

Air date: 1999-02-18

Runtime: min

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

Air date: 1999-02-25

Runtime: min

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

Air date: 1999-03-04

Runtime: min

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

Air date: 1999-03-11

Runtime: min

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

Air date: 1999-04-22

Runtime: min

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.

Air date: 1999-05-06

Runtime: min

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

Air date: 1999-07-01

Runtime: min

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

Air date: 1999-07-08

Runtime: min

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

Air date: 1999-07-15

Runtime: min

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

Air date: 1999-07-22

Runtime: min

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

Air date: 1999-07-29

Runtime: min

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

Air date: 1999-08-05

Runtime: min

1. Ricky Schroder vs. Gary Coleman 2. Lauryn Hill vs. Shania Twain 3. Hugh Grant vs. All-comers [ Clint Eastwood, Harvey Keitel, & Andy Dick ]

Air date: 1999-10-07

Runtime: min

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

Air date: 1999-10-14

Runtime: min

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

Air date: 1999-10-21

Runtime: min

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

Air date: 1999-10-28

Runtime: min

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

Air date: 1999-11-04

Runtime: min

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

Air date: 1999-11-11

Runtime: min

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