| 1 | Chyna defeats Crash Holly Singles Match DX's Chyna defeated Crash Holly in a brief but dominant encounter on the final Raw Is War of 1999. | Crash Holly | Chyna | Singles Match |
| 2 | The Dudley Boyz defeat The Acolytes, Edge & Christian and D'Lo Brown & The Godfather – Fatal 4-Way Match Fatal 4-Way Match Bubba Ray and D-Von Dudley won a Fatal 4-Way tag match by defeating the Acolytes, Edge and Christian, and D'Lo Brown and the Godfather — a significant result for the Dudley Boyz heading into the new millennium. | The Acolytes, Edge & Christian, D'Lo Brown & The Godfather | The Dudley Boyz (Bubba Ray & D-Von Dudley) | Fatal 4-Way Match |
| 3 | Kurt Angle defeats The Headbangers – 2-on-1 Handicap Match 2-on-1 Handicap Match The Olympic gold medalist Kurt Angle demonstrated his extraordinary ability by defeating both Mosh and Thrasher of the Headbangers simultaneously in a 2-on-1 Handicap Match — an impressive final statement of 1999 from the future major champion. | The Headbangers (Mosh & Thrasher) | Kurt Angle | 2-on-1 Handicap Match |
| 4 | Chris Jericho retains WWF IC Championship vs. Al Snow via DQ WWF Intercontinental Championship IC Champion Chris Jericho retained his title when Al Snow was disqualified, the eccentric challenger unable to win the championship through rule-breaking. | Al Snow | Chris Jericho (c) via DQ | WWF Intercontinental Championship |
| 5 | The Rock defeats Mankind – Pink Slip on a Pole Match Pink Slip on a Pole Match The People's Champion The Rock defeated Mankind in a Pink Slip on a Pole Match — one of Raw Is War's more creative stipulation concepts, with the loser being 'fired'. The result was a significant moment in the Rock's ongoing ascent. | Mankind | The Rock | Pink Slip on a Pole Match |
| 6 | Prince Albert & Ivory defeat Val Venis & The Kat, Viscera & Jacqueline and Gangrel & Luna Vachon – Fatal 4-Way Match Fatal 4-Way Mixed Tag Match Prince Albert and Ivory defeated three other mixed tag teams in a Fatal 4-Way encounter. | Val Venis & The Kat, Viscera & Jacqueline, Gangrel & Luna... | Prince Albert & Ivory | Fatal 4-Way Mixed Tag Match |
| 7 | X-Pac defeats Jeff Hardy Singles Match DX's X-Pac defeated the young Jeff Hardy in a fast-paced encounter between two of Raw Is War's most athletically gifted performers. | Jeff Hardy | X-Pac | Singles Match |
| 8 | Test defeats Kane via DQ Singles Match Test was awarded a DQ victory over Kane on the final Raw Is War of the millennium. | Kane | Test via DQ | Singles Match |
| 9 | The New Age Outlaws retain WWF Tag Team Championship vs. Too Cool WWF World Tag Team Championship Road Dogg and Billy Gunn retained the WWF Tag Team Championship against the crowd-pleasing Too Cool — Scotty 2 Hotty and Grandmaster Sexay — in the final tag title defence of 1999. | Too Cool (Scotty 2 Hotty & Grandmaster Sexay) | The New Age Outlaws (c) | WWF World Tag Team Championship |
| 10 | Big Show retains WWF Championship vs. Triple H WWF Championship WWF Champion Big Show closed the final Raw Is War of the 1990s by retaining the WWF Championship against Triple H — a fitting close to an extraordinary year that had seen multiple championship changes, landmark debuts, and the full flowering of the Attitude Era. The WWF entered the new millennium as the undisputed leader of professional wrestling entertainment. | Triple H | Big Show (c) | WWF Championship |