The WWE Championship is the most prestigious championship that has been in operation since 1963. Nature Boy Buddy Rogers was the first man to hold the WWE Championship. Nevertheless, no fewer than 11 WWE Championship title changes took place in 1999. WWE had several main eventers at the top of their games, and many wrestlers won the WWE Championship for the first time in their careers that year.
It was the second time in three years that the WWE Championship changed hands at all four of the significant "Big Four" events. A WWE Title change happened on SmackDown for the first time in 1999, and there were multiple WWE Championship title changes on Raw. Mankind defeated The Rock for the WWE Championship on the January 4, 1999 taping of Raw but since it technically took place in December 1998 it will not be included in this list.
11 Mr. McMahon Defeats Triple H - SmackDown (9/16)
Mr. McMahon was bidding to become the oldest WWE Champion in history when he challenged his future son-in-law Triple H for the title on the September 16, 1999 taping of SmackDown. Triple H was the overwhelming favorite to prevail and McMahon wore the proverbial crimson mask.
McMahon shouldn't have been in this match as he was supposed to be banished from WWE programming for the foreseeable future after the stipulations at Fully Loaded. Nonetheless, McMahon received an unlikely assist from Steve Austin, and McMahon beat Triple H to become WWE Champion at 54.
10 Big Show Defeats Triple H And The Rock - Survivor Series
At Survivor Series 1999, Triple H was scheduled to defend the WWE Championship against Steve Austin and The Rock but Austin's neck issues flared up. Big Show pulled double duty and he replaced Austin to ensure that Triple H would still defend the WWE Championship in a triple threat match.
The match was average and could have been miles better than it was. Mr. McMahon interfered and he clocked Triple H in the face with the WWE Championship. Show covered Triple H with McMahon counting Triple H's shoulders down and Show became WWE Champion for the first time.
9 The Undertaker Defeats Steve Austin - Over The Edge
Owen Hart's untimely passing overshadowed everything that happened at Over the Edge 1999. The main event featured Steve Austin and The Undertaker going head-to-head with the WWE Championship at stake, and Shane McMahon was the special guest referee.
It's well documented that Austin and Undertaker's matches never clicked and this was a boring match between the pair. Mr. McMahon eventually fulfilled his duties as the second special guest referee, but the Deadman secured his third WWE Championship with Shane fast counting Austin's shoulders down.
8 Mankind Defeats The Rock - Halftime Heat
The filler feud between Mankind and The Rock in the Attitude Era was outstanding. The WWE Championship was like a yo-yo, and Mankind attempted to reclaim the WWE Title from The Rock in a unique empty arena match on Halftime Heat.
This was a fantastic match between the pair and it's not easy to pull off a successful match without a crowd. Mankind got the upper hand and he applied the Mandible Claw with Rock incapacitated. Rock was defenseless as a forklift came down on him and Mankind covered him to kickstart his second run as WWE Champion.
7 Triple H Defeats Mankind - Raw (8/23)
Triple H continued his quest to become WWE Champion for the first time in his career, and 24 hours removed from SummerSlam, Triple H challenged his old rival Mankind for the WWE Championship. Shane McMahon oversaw proceedings as the special guest referee.
This was a competitive WWE Championship match and Triple H had a determined look in his eyes to get the job done. Mankind gave it his best shot but the Pedigree was enough for Triple H to begin his love affair with the WWE Championship.
6 Triple H Wins The Vacant WWE Championship In A Six Pack Challenge - Unforgiven
Mr. McMahon vacated the WWE Championship, and that left Triple H, Kane, Big Show, The Rock, Mankind, and The British Bulldog to slug it out in a six-pack challenge at Unforgiven 1999. Steve Austin was the special enforcer, and this main event was a superb contest.
Triple H, Kane, Rock, and Mankind had won the WWE Championship before and they were looking to climb the mountaintop again. Bulldog hit Rock with a chair, and Triple H executed the Pedigree on Rock with Austin reluctantly awarding Triple H the WWE Championship.
5 Mankind Defeats Steve Austin And Triple H - SummerSlam
Jesse "The Body" Ventura was the special guest referee in a mouthwatering triple threat match for the WWE Championship involving Steve Austin, Triple H, and Mankind. "The Body" didn't hesitate to send Chyna back to the locker room to ensure that the match remained fair.
Triple H had his chances to win the WWE Championship but it failed to materialize. Mankind surprisingly clinched the WWE Championship for the third time after he put Austin away with a Double-Arm DDT.
4 Steve Austin Defeats The Undertaker - Raw (6/28)
Steve Austin put a clause in his contract when he was the CEO of WWE to have a future WWE Championship match. On the night after King of the Ring 1999, the Texas Rattlesnake challenged The Undertaker for the gold
They drew good ratings and the atmosphere was fantastic in this titular bout. Undertaker pushed Austin to his limit but Austin saw off Undertaker with a stunner to become a four-time WWE Champion.
3 The Rock Defeats Mankind - Raw (2/15)
The Rock and Mankind's WWE Championship matches were physical encounters and it was no different on the February 15, 1999 episode of Raw. The Corporate Champion was seeking a third WWE Championship reign, and he was looking to cement his spot in the main event of WrestleMania 15, but he had to go through Mankind in a ladder match.
Neither competitor was a ladder match specialist but they produced a remarkable match. Rock put Mankind through the announce table with a Rock Bottom, and Steve Austin had a closer look at the action at the commentary table. Ultimately, Paul Wight interfered and he chokeslammed Mankind off the ladder which allowed Rock to retrieve the WWE Championship.
2 The Rock Defeats Mankind - Royal Rumble
Mankind and The Rock were adversaries on the third successive North American pay-per-view in a row and they clashed in an "I Quit" match for Mankind's WWE Championship at the 1999 Royal Rumble. This was a violent match, and Mankind took a tremendous amount of punishment.
He was on the receiving end of several sickening chair shots to the head. Mankind's family was in attendance to watch it unfold. Mrs. Foley's Baby Boy had some offense of his own, but Rock recaptured the WWE Championship with a recording of Mankind uttering the words "I Quit."
1 Steve Austin Defeats The Rock - WrestleMania 15
WrestleMania 15 featured Steve Austin and The Rock's first of three blockbuster WrestleMania clashes. Rock entered as the reigning WWE Champion but Austin overcame several obstacles to book his WWE Title match with Rock and he wasn't going to let this opportunity pass him by.
Rock was close to retaining the gold but Austin kicked out of the Rock Bottom. Rock showcased his resiliency as he kicked out of the stunner. Nonetheless, despite Rock's efforts, it was inevitable that Austin would walk out of WrestleMania 15 with the WWE Championship in his possession.