|Monday Night Raw|
|Date||December 27, 1999|
|City||Greensboro, North Carolina|
|Previous episode||December 20, 1999|
|Next episode||January 3, 2000|
The December 27, 1999 Edition of RAW is a Professional wrestling television show of the WWE's RAW brand, which took place on December 27, 1999 at the Greensboro Coliseum in Greensboro, North Carolina.
- Numbers in parentheses indicate the length of the match.
- (c) refers to the champion(s) heading into the match.
- Chyna (w/ The Kat) defeated Crash Holly (w/ Hardcore Holly) (1:15)
- The Dudley Boyz (Buh Buh Ray Dudley & D-Von Dudley) defeated D-Lo Brown & The Godfather and Christian & Edge and The Acolytes (Bradshaw & Faarooq) in a Four Corners Tag Team Match (with Joey Abs as Special guest referee) (2:33)
- Kurt Angle defeated The Headbangers (Mosh & Thrasher) in a Two On One Handicap Match (1:00)
- Al Snow defeated Chris Jericho (c) by DQ in a WWF Intercontinental Championship Match (1:15)
- The Rock defeated Mankind in a Pink Slip On A Pole Match (6:11)
- Ivory & Prince Albert defeated Gangrel & Luna, and Jacqueline & Viscera and The Kat & Val Venis in a Inter Gender Four Corners Tag Team Match (2:02)
- X-Pac defeated Jeff Hardy (w/ Matt Hardy & Terri) (4:05)
- Test defeated Kane (w/ Tori) by DQ (2:59)
- The New Age Outlaws (Mr. Ass & The Road Dogg) (w/ X-Pac) (c) defeated Too Cool (Grandmaster Sexay & Scotty 2 Hotty) (w/ Rikishi Phatu) to retain the WWF Tag Team Championship (2:45)
- The Big Show (c) defeated Triple H (w/ Stephanie McMahon-Helmsley) to retain the WWF Championship (5:56)