The wrestling career of Sycho Sid is outstanding. Not a lot of wrestlers can say that they have won the WWE Championship and the WCW World Heavyweight Championship twice. Sid also has the distinction of being the only man to beat Shawn Michaels and Bret Hart for the WWE Championship, which is another underrated achievement. Nevertheless, Sid isn't an in-ring technician by any stretch of the imagination, but he knows how to captivate an audience.
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The most successful run in Sid's WWE career was in late 1996 until he departed from the company in the summer of 1997. He headlined WrestleMania for the second time, and he battled against some of the all-time greats in his final batch of matches on a WWE pay-per-view. These bouts showcased the very best and worst of the two-time WWE Champion.
10 Sycho Sid Vs. The British Bulldog - SummerSlam 1996
Sycho Sid battled The British Bulldog at SummerSlam 1996. Chants of "Sycho Sid" reverberated around the arena, which showcased his popularity. Sid got the upper hand and Bulldog retreated to the outside. Clarence Mason made his way down the aisle, giving Bulldog some support.
Bulldog managed to fight back and he clotheslined Sid over the top rope. He continued his aggression, and he connected with his patented powerslam. However, Bulldog was distracted by Mason and Jim Cornette's bickering on the outside. Sid recovered and nailed Bulldog with a chokeslam, and he followed it up with a Powerbomb to prevail in a lackluster bout.
9 Sycho Sid Vs. Vader - In Your House: Buried Alive, 1996
The winner of Sycho Sid and Vader's match at In Your House: Buried Alive would go on to face Shawn Michaels for the WWE Championship a month later at Survivor Series 1996. HBK undertook commentary duties to take a closer look at his potential next challenger. Vader's manager Jim Cornette repeatedly got involved, and he clocked Sid with his tennis racquet on the outside.
Vader caught Sid from the top rope with ease and he splashed him but Sid kicked out. Moreover, Sid attempted to plant Vader with a Powerbomb a couple of times but he failed to pull it off. Nonetheless, Sid booked his date with Michaels at Survivor Series as he saw off Vader with a chokeslam.
8 Sycho Sid & The 1-2-3 Kid Vs. Razor Ramon & Marty Jannetty - In Your House: Seasons Beatings, 1995
Sycho Sid and The 1-2-3 Kid represented Ted DiBiase's Million Dollar Corporation in a tag team match against the Intercontinental Champion Razor Ramon and Marty Jannetty at In Your House: Seasons Beatings. This bout opened up the show, and it was better than many expected it to be.
The 1-2-3 Kid was fortunate to have Sid on his side, and Sid got himself involved in proceedings. The Million Dollar Corporation dominated the majority of the match. However, the Bad Guy attempted to showcase his strength by trying to finish off Sid with the Razor's Edge. That failed to materialize but Ramon and Jannetty managed to pick up the win.
7 Sycho Sid Vs. The Undertaker - WrestleMania 13
Five years after his first WrestleMania main event, Sycho Sid was in a WrestleMania main event once again at WrestleMania 13. This time, Sid was the reigning WWE Champion and he put his championship on the line against The Undertaker in a No Disqualification match.
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Unfortunately, this match was dreadful, and it showed Sid's inability to wrestle in long matches. Bret Hart repeatedly interfered, and Shawn Michaels was on commentary. Ultimately, the Deadman put Sid away with a Tombstone Piledriver to score his second WWE Championship win in his maiden WrestleMania main event appearance.
6 Wildcard Match - Survivor Series 1995
Strange bedfellows were formed in the Wildcard match at Survivor Series 1995 with rivals, babyfaces, and heels on the same team. Sid teamed up with Shawn Michaels, The British Bulldog, and Ahmed Johnson. Their opponents were Razor Ramon, Dean Douglas, and former two-time WWE Tag Team Champions Owen Hart and Yokozuna.
Sid was on the apron for large portions of the match. Michaels blind-tagged Sid, and he overpowered Ramon with ease. Sid chokeslammed Razor, and Sid held Razor for Michaels to execute the Sweet Chin Music. However, HBK accidentally nailed Sid with it. The Bad Guy took advantage, and he eliminated him from the match.
5 Sycho Sid & The Legion Of Doom Vs. The Hart Foundation - King Of The Ring 1997
There was an electric atmosphere in the six-man tag team match featuring Sycho Sid and the Legion Doom who went to battle with the Hart Foundation's Jim Neidhart, Intercontinental Champion Owen Hart, and the European Champion The British Bulldog at King of the Ring 1997. Sid and LOD isolated Owen in the early proceedings of the contest.
Surprisingly, the match was fast-paced, considering who was in the match. Nevertheless, the Hart Foundation eventually asserted their authority. However, Sid chokeslammed Bulldog and he was going to powerbomb him but Owen was the legal man, and he executed the sunset flip to steal the win.
4 Sycho Sid Vs. Shawn Michaels - Royal Rumble 1997
Sycho Sid defended the WWE Championship against Shawn Michaels at the 1997 Royal Rumble in the main event. Sid had to contend with a partisan crowd as the Heartbreak Kid had the hometown support with the Rumble taking place in the Alamodome in San Antonio, Texas.
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This match could have been miles better but HBK was suffering from a bout of flu, but he was always going to participate. Sid gave it his all, but Michaels recaptured the WWE Championship at the first attempt which sent the crowd into euphoria.
3 Sycho Sid, Shawn Michaels, And Ahmed Johnson Vs. Camp Cornette - In Your House: International Incident, 1996
Sycho Sid teamed up with the WWE Champion Shawn Michaels and Intercontinental Champion Ahmed Johnson in a six-man tag team match at In Your House: International Incident against Camp Cornette comprised of Vader, Owen Hart, and The British Bulldog.
Michaels did a good job of carrying Sid and Johnson through this match, which made the match watchable. However, it was the Mastodon who earned a handy pinfall win over Michaels with the Vader Bomb, which led to Vader challenging Michaels for the WWE Championship at SummerSlam 1996.
2 Sycho Sid Vs. Bret Hart - In Your House: It's Time, 1996
Bret Hart was back in WWE Championship contention and he challenged Sycho Sid for the title at In Your House: It's Time. Shawn Michaels wasn't far away from the action as he was at the broadcast table commentating on the match. This was another solid match from Sid, and he hung with the Hitman every step of the way.
Sid looked like he belonged in the WWE Title picture, and Michaels could not resist getting involved in the match. Even Steve Austin got involved in the heated WWE Championship match but Owen Hart and The British Bulldog prevented Bret from receiving further damage. Despite the chaos, Sid remained cool and he retained the WWE Championship which led to Bret assaulting Michaels after the bout.
1 Sycho Sid Vs. Shawn Michaels - Survivor Series 1996
One of the best matches in Sycho Sid's career, saw him challenging Shawn Michaels for the WWE Championship at Survivor Series 1996. This bout took place in the hallowed halls of Madison Square Garden, and despite being the heel, Sid got the backing from the fans.
Michaels works well with larger guys, and this was another match where Michaels showcased his brilliance. For sure, HBK was overpowered but he kept Sid at bay. Ultimately, Sid ended Michaels' 231-day reign as WWE Champion with a jaw-dropping Powerbomb, which led to Sid kickstarting his first run as WWE Champion.
