The December 16, 1999 Edition of Smackdown is a Professional wrestling television show of the WWF's Smackdown brand, took place on December 14, 1999 in Tallahassee, Florida at the Florida State University.
- Numbers in parentheses indicate the length of the match.
- (c) refers to the champion(s) heading into the match.
- Chris Jericho (c) defeated Prince Albert to retain the WWF Intercontinental Championship (2:44)
- Kurt Angle defeated Test by DQ (2:53)
- Matt Hardy defeated Jeff Hardy (5:23)
- X-Pac defeated Tori (0:43)
- Mankind defeated Al Snow in a Falls Count Anywhere Match (8:01)
- Edge defeated Christian (3:54)
- The Acolytes (Bradshaw & Faarooq) defeated The Mean Street Posse (Joey Abs, Pete Gas & Rodney) in an Acolytes Rules Two On Three Handicap Match (0:26)
- Rikishi & Too Cool (Grandmaster Sexy & Scotty 2 Hotty) defeated The Hollys (Crash Holly & Hardcore Holly) & Viscera (6:08)
- The New Age Outlaws (Mr. Ass & The Road Dogg) (c) defeated Gerald Brisco & Pat Patterson to retain the WWF Tag Team Championship (2:00)
- The Big Show vs. The Rock ended in a no contest in a WWF Championship Lumberjack Match (6:42)