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21 Episodes 1999 - 1999
Episode 1
Sun, Jan 31, 199921 mins
In the season 2 premiere, Dolly Parton and Jennifer Lopez size each other up; Michael Jackson tries to take over Madonna's half-time show; Evander Holyfield and Mike Tyson fight for the World Heavyweight Champion belt.

Episode 2
Thu, Feb 4, 199921 mins
Ice-Cube and Ice-T try to kill each other in cold blood; Al Pacino and Robert De Niro unleash their killer alter egos, with referee Marlon Brando; The Backstreet Boys face off against the Beastie Boys in a robot war of epic proportion.
Episode 3
Thu, Feb 11, 199921 mins
Calista Flockhart and Lucy Lawless compete for Woman of the Year; Unearthed footage reveals a fight between Don Johnson and Culture Club's Boy George; Penn and Teller engage in a spellbinding fight against Siegfried and Roy.
Episode 4
Thu, Feb 18, 199921 mins
Jennifer Aniston, Lisa Kudrow and Courteney Cox are Friends no more; Sean Connery and Roger Moore vie for the title of the Baddest Bond; Genghis Khan and Mahatma Gandhi are summoned into the ring.
Episode 5
Thu, Feb 25, 199921 mins
The story of Moses and the Pharaoh gets a brutal re-telling; Larry King and Geraldo Rivera take part in a Live Kick-Ass Call-In; Neve Campbell and Sarah Michelle Gellar enter a battle of the Teen Scream Queens.
Episode 6
Thu, Mar 4, 199921 mins
Paul Hogan and Mel Gibson take their fight down under; Antonio Banderas prepares to put Cheech Marin in a permanent siesta; World War 3 erupts between Fabio, Bono, and Yoko Ono.
Episode 7
Thu, Mar 11, 1999
Models Kate Moss, Tyra Banks, and Claudia Schiffer take to the Deathmatch catwalk; Busta Rhymes enters a poetry slam with legendary bard William Shakespeare; The Real World's Jon, Tami, Jacinda, and Puck throw down.
Episode 8
Thu, Apr 22, 199921 mins
As the show prepares for its first movie, Oliver Stone and Martin Scorsese fight for director's role; John Wayne and Groucho Marx's feud is unearthed from the vault; Cameron Diaz and Meryl Streep star in a savage showdown.
Episode 9
Thu, May 6, 199921 mins
Emeril Legasse challenges the Two Fat Ladies to a killer cook-off; MTV's Matt Pinfield and Jesse Camp find out who's the better VJ; Pat Sajak and Alex Trebek enter into a deadly quiz show, where their lives are the top prize.
Episode 10
Thu, Jul 1, 199921 mins
The grudge between Bill Clinton and Kenneth Starr finally comes to a head; James Van Der Beek declares war against dictator Saddam Hussein; George Washington and Abraham Lincoln decide which is the best president.
Episode 11
Thu, Jul 8, 199921 mins
Charlie Sheen and Emilio Estevez take their sibling rivalry into the ring; Donny and Marie Osmond sink their teeth into Julia and Eric Roberts; Bob and Jakob Dylan tangle with Jerry and Ben Stiller in a father-son brawl.
Episode 12
Thu, Jul 15, 199921 mins
Ron Jeremy takes on Tommy Lee in a celebrity cock-fight; Alanis Morissette and Jewel engage in a ladder match for charity; The Three Tenors challenge the Three Stooges in a culture clash.
Episode 13
Thu, Jul 22, 199921 mins
Dennis Miller battles Carrot Top in "Props vs. Satire." Rodney Dangerfield faces Don Rickles in a battle of insults in a ring with a giant grill, guaranteeing an actual celebrity "roast." Main event: Billy Crystal vs. Robin Williams vs. Whoopi Goldberg.
Episode 14
Thu, Jul 29, 199921 mins
Snubbed Ozzy Osbourne seeks grievance from the knighted Elton John; Martha Stewart sets to re-decorate the ring with Sandra Bernhard's blood; Nice-guy Tom Hanks toughens up to take on moody Sean Penn.
Episode 15
Thu, Aug 5, 199921 mins
Former child stars Rick Schroder and Gary Coleman release pent-up frustration on each other; Lauryn Hill and Shania Twain fight to lose their Mainstream Artist title; Hugh Grant enters a Hollywood Tough Man contest against all comers.
Episode 16
Thu, Oct 7, 199921 mins
Dennis Franz seeks vengeance against Sammo Hung; Fast-talking comedian Chris Tucker faces off against slower-paced Steven Wright; Gwyneth Paltrow dukes it out with Winona Ryder in the Dome of Devastation.
Episode 17
Thu, Oct 14, 199921 mins
Bette Midler and Cher compete in the sequel to the World's Deadliest Divas; Roberto Benigni faces the wrath of tyrant Benito Mussolini; John Travolta and Nicolas Cage literally Face/Off in the ring.
Episode 18
Thu, Oct 21, 199921 mins
A clip show featuring interviews from Celebrity Deathmatch fans from around New York, requesting their favorite fights from the past two seasons, and sharing their general knowledge about the show.
Episode 19
Fri, Oct 8, 199921 mins
Horror icons Frankenstein's Monster and the Wolfman meet in a graveyard smash; Guest spectator The Undertaker saves Nick Diamond's son from a demon; Rockers KISS enter a deadly contest competition with 'NSync.
Episode 20
Thu, Nov 4, 199921 mins
Richard Simmons and Billy Blanks host a killer workout regime; Don King and Donald Trump wage war, with the loser paying in blood; Keanu Reeves and Brad Pitt lead in a virtual-reality showdown.
Episode 21
Thu, Nov 11, 199921 mins
By fan's request: Ben Affleck and Matt Damon put their inventive skills to deadly use; Ozzy Osbourne returns to face Rob Zombie in the Deathmatch from Hell; Marilyn Manson's live performance is interrupted by Ricky Martin.