| 1 | X-Pac def. Hardcore Holly via DQ Quarterfinal Match X-Pac advanced to the semifinals after Hardcore Holly was disqualified at 3:02 for attacking X-Pac with a steel chair. | 3:02 | Hardcore Holly | X-Pac (via DQ) | King of the Ring Quarterfinal |
| 2 | Kane def. Big Show Quarterfinal Match Kane defeated Big Show at 6:36 after hitting him over the head with a steel chair to advance to the semifinals. | 6:36 | Big Show | Kane | King of the Ring Quarterfinal |
| 3 | Billy Gunn def. Ken Shamrock Quarterfinal Match Billy Gunn advanced to the semifinals by defeating the 1998 King of the Ring, Ken Shamrock, at 3:34 after the referee stopped the match due to Shamrock spitting blood from a storyline injury. | 3:34 | Ken Shamrock | Billy Gunn | King of the Ring Quarterfinal |
| 4 | Road Dogg def. Chyna Quarterfinal Match Road Dogg defeated Chyna at 13:19 to advance after countering a low blow attempt into a pumphandle drop. | 13:19 | Chyna | Road Dogg | King of the Ring Quarterfinal |
| 5 | The Hardy Boyz def. The Brood (Edge & Christian) Tag Team Match In a showcase of future tag team legends, Matt and Jeff Hardy (with Michael Hayes) defeated Edge and Christian at 4:49 when Jeff pinned Edge after a Twist of Fate from Matt. | 4:49 | — | — | Tag Team Match |
| 6 | Billy Gunn def. Kane Semifinal Match Billy Gunn defeated Kane at 5:25 following a distraction by Big Show, who attacked Kane with a steel chair, allowing Gunn to score the pin. | 5:25 | Kane | Billy Gunn | King of the Ring Semifinal |
| 7 | X-Pac def. Road Dogg Semifinal Match In a D-Generation X friendly match, X-Pac defeated Road Dogg at 3:08 with an X-Factor to advance to the finals. | 3:08 | Road Dogg | X-Pac | King of the Ring Semifinal |
| 8 | The Undertaker (c) def. The Rock WWF World Heavyweight Championship Match The Undertaker (with Paul Bearer) retained the WWF Championship against The Rock at 19:10 after Triple H interfered and hit The Rock with a Pedigree, allowing Undertaker to hit a Tombstone for the win. | 19:10 | The Rock | The Undertaker (retained) | WWF World Heavyweight Championship Match |
| 9 | Billy Gunn def. X-Pac King of the Ring Final Billy Gunn defeated X-Pac at 5:33 following a Fameasser off the top rope to be crowned the 1999 King of the Ring. | 5:33 | X-Pac | Billy Gunn | King of the Ring Tournament Final |
| 10 | Vince McMahon & Shane McMahon def. Stone Cold Steve Austin Main Event — Handicap Ladder Match for 100% Control of the WWF Vince and Shane McMahon defeated Stone Cold Steve Austin in a 2-on-1 Handicap Ladder Match at 17:11. Just as Austin was about to retrieve the briefcase, an unseen force (storyline mystery) raised the briefcase out of his reach. Shane then knocked Austin off the ladder and retrieved it, winning full ownership of the WWF for the McMahons. | 17:11 | Stone Cold Steve Austin | — | Handicap Ladder Match |