The Attitude Era was heating up in 1999 with WWE starting to dominate the Monday Night Wars. Stone Cold Steve Austin vs. Mr. McMahon was just part of it, as names like The Rock, Triple H, Undertaker, Mankind and Kane were all rising to the top of the roster.
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The year started crazy, with the feud between Mr. McMahona and Stone Cold Steve Austin still on fire, and the year ended with more twists and turns than any year in WWE history. Here is a look at all 13 main events from the pay-per-views that WWE held during the Attitude Era in 1999, ranked.
13 SURVIVOR SERIES: TRIPLE H VS. THE ROCK VS. BIG SHOW
The main event at Survivor Series in 1999 was supposed to be WWE Champion Triple H defending his title against The Rock and Stone Cold Steve Austin. However, early in the PPV, a car ran down Austin in the parking garage, and Big Show replaced him in the main event. The match had several run-ins, and it ended with Mr. McMahon hitting Triple H with the championship, and Big Show pinned him to become the new world champion.
12 ROYAL RUMBLE - RUMBLE MATCH
The Royal Rumble was the first PPV of 1999 and featured a match that opened with the hottest feud in WWE at the time. Stone Cold Steve Austin was the first entrant, and Mr. McMahon was the second man in the match. Sadly, the two men most fans wanted to see fought out of the ring and out of the arena area. Then, at the end of the match, both men returned, and McMahon eliminated Austin to win the Royal Rumble.
11 KING OF THE RING: STEVE AUSTIN VS. VINCE MCMAHON & SHANE MCMAHON
At King of the Ring 1999, the main event saw Stone Cold Steve Austin take on not only Mr. McMahon but his son Shane McMahon, in a ladder match. This match came after McMahon revealed himself as the Higher Power and leader of the Corporate Ministry.
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Linda McMahon made Austin the new CEO of WWE, and this match was for that role in the company. Someone raised the briefcase out of Austin's reach when he tried to retrieve it, and Shane McMahon went on to get it in the end.
10 OVER THE EDGE: STEVE AUSTIN VS. THE UNDERTAKER
The main event of Over the Edge 1999 had a somber edge to it. This was the PPV where Owen Hart fell to his death in the ring. The storyline for this main event was dark anyway, as Undertaker had abducted Stephanie McMahon and hung her from his symbol. Austin was fighting the good fight and ended up defending his title against Undertaker. Due to several run-ins, Undertaker ended up pinning Austin and winning the title.
9 FULLY LOADED: STEVE AUSTIN VS. THE UNDERTAKER
This match followed King of the Ring, where Stone Cold Steve Austin lost his power as CEO to Mr. McMahon in a ladder match. However, before Austin lost his power, he had already written up a contract where he ensured he would fight Undertaker for the WWE Title at Fully Loaded.
The match was a First Blood match, and if Austin won, McMahon would never appear on TV again. There was lots of interference, and X-Pac caused Undertaker to bleed, giving Austin the win and the title, and removing McMahon from television.
8 ARMAGEDDON: TRIPLE H VS. VINCE MCMAHON
The last PPV of 1999 for WWE saw Triple H in a war with his father-in-law Mr. McMahon. The two were in a heated feud that included everything from DX accusing McMahon of trying to kill them to Triple H hijacking Stephanie McMahon and Test's wedding. The match was No Hold's Barred, and it ended with Stephanie turning on her father and distracting him, to help Triple H win, and the McMahon-Helmsley era began.
7 NO MERCY: TRIPLE H VS. STEVE AUSTIN
No Mercy 1999 was the show where Vince Russo left the company beforehand, and WWE moved on without him. The previous nine months saw several world title changes, and at this time, it was Triple H on top as the champ with Austin as the challenger. This was an anything goes match and ended when The Rock ran in and tried to hit Triple H with the sledgehammer, missed, and smashed Austin, allowing Triple H to walk out as the winner.
6 REBELLION: TRIPLE H VS. THE ROCK
The main event at Rebellion in 1999 was a steel cage match that saw Triple H defend his title against The Rock. Much like most main event matches in this year of the Attitude Era, there was non-stop interference. The first man out was British Bulldog, who kept Rock from escaping the ring. The second was Chyna, who also stopped Rock. This allowed Triple H to escape the cage and retain his title.
5 SUMMERSLAM: STEVE AUSTIN VS. TRIPLE H VS. MANKIND
The main event at SummerSlam included the almost year-long feud between Triple H and Stone Cold Steve Austin, but it also added Mankind into the mix. Austin had won the WWE Championship from Undertaker at Fully Loaded, and Triple H beat The Rock to become the number one contender.
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Jesse "The Body" Ventura was named the special guest referee for the match. In a strange twist, Chyna accidentally beat Triple H for the number one contender spot, and then Mankind beat her for the spot. Eventually, Triple H and Mankind ended up pinning each other in another match, and both men challenged Austin, with Mankind picking up the surprise win and the title.
4 ST. VALENTINE'S DAY MASSACRE: STEVE AUSTIN VS. VINCE MCMAHON
The Stone Cold Steve Austin feud with Mr. McMahon hit its high spot in this match from St. Valentine's Day Massacre 1999. It was a steel cage match, ensuring that no one could help McMahon. What resulted was Austin destroying McMahon in a match where the main event at WrestleMania was on the line. Big Show made his WWE debut in this match, but he threw Austin into the cage, and it collapsed, with Austin landing outside for the win.
3 BACKLASH: STEVE AUSTIN VS. THE ROCK
Some of the best matches in WWE history featured Stone Cold Steve Austin vs. The Rock. However, while people look at their WrestleMania trilogy, there were others, including one at Backlash 1999. Austin had beaten The Rock at WrestleMania XV for the WWE Title, and this was a No Hold's Barred rematch for the title. Shane McMahon was the referee, but Mr. McMahon returned and hit his son with the title to allow Austin to get the Stunner and a win over The Rock.
2 WRESTLEMANIA XV: THE ROCK VS. STONE COLD STEVE AUSTIN
The Rock and Stone Cold Steve Austin had three amazing WrestleMania matches. Austin won the first two while The Rock finally got his win in their third, which was also the end of Austin's career. The match was No DQ, and the two fought for 16 minutes before Austin hit the Stunner and won the WWE Championship after Mankind ran out in a referee uniform to stop Mr. McMahon from helping The Rock win.
1 UNFORGIVEN - VACANT WWF TITLE, SIX-PACK CHALLENGE
The best Attitude Era PPV main event from 1999 took place at Unforgiven, and it didn't even include Stone Cold Steve Austin as a wrestler. Instead, the WWE Championship was vacant, and six men fought for it — Triple H, The Rock, British Bulldog, Big Show, Kane, and Mankind.
There were shenanigans because WWE referees were on strike, and they showed up to interfere with Jim Korderas crossing the picket line to officiate the match. Triple H ended up winning when Austin showed up at the end and acted as the referee.
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