Fans in the WWE know that win-loss records do not really matter. Winning championships and proving yourself in the ring can go a long way for a Superstar no matter how many times they lost. It still doesn't make it any less surprising to see when a random WWE Superstar or guest star gets a victory on the show. It's often entertaining to see the following performers in a WWE ring, but nobody expected any of the following people to actually get a win for the record books. This is especially true when the performers are competing against Superstars like John Cena, The Big Show, Ted DiBiase, and Stardust, among others.
The following fifteen performers probably shouldn't have been actively competing in a WWE match, let alone winning one. The winning moment was usually a ploy to shock the WWE Universe, move stories forward, and create scenes that fans and mainstream media would talk about for weeks. These victories occurred on shows that included WWE Raw, SmackDown, and pay per view events like WrestleMania. The list of outcasts includes celebrity guest stars, legendary managers, and some pro wrestlers that you never expected to see in a WWE ring again.
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Britney Spears' ex-husband went through a brief streak of fame back in 2006 and 2007. It was during this time that the wannabe "rapper" began appearing on WWE programming. After taunting and interfering in multiple John Cena matches, the two would compete in a one-on-one battle in the main event of WWE Raw.
The match took place on New Year's Day and apparently K-Fed got his resolution by defeating John Cena cleanly in the ring. Sure, K-Fed got a little help from John Morrison, but a victory is a victory and it doesn't get much bigger than defeating John Cena. Despite his main event win, K-Fed never wrestled again and divorced from Spears just weeks after the match aired. John Cena quickly brushed off this loss, but it's definitely a terrible blemish on his Hall of Fame career.
In the late 1990s, Goldberg was the hottest commodity in pro wrestling. WWE's answer to WCW's unstoppable monster was Gillberg... a skinny and frail jobber that openly mocked Goldberg on a weekly basis. Before becoming Gillberg, Duane Gill was already having a bad losing streak except for a single win against Christian for the Light Heavyweight Championship. After weeks of getting dominated in the ring, no one expected Gillberg to ever get a victory. This all changed on a 1999 episode of WWE Raw when he defeated Goldust thanks to the help of The Blue Meanie.
The victory would be short-lived as Gillberg went back to his losing streak, despite holding the Light Heavyweight Championship that he rarely defended. As Goldberg's popularity wore off in WCW, Gillberg was quietly written off TV.
13 Eric Bischoff
Eric Bischoff shocked the WWE Unvierse when he debuted as the General Manager of WWE Raw. While Bischoff was a powerful leader in the WWE, not many people expected much when it came to his in-ring skills. In an effort to keep his job, Bischoff was forced into a match against Stone Cold Steve Austin. While the outcome of that match was obvious, no one knew what to expect during his “warm-up” match against Jim Ross.
In a shocking move, Bischoff began completely destroying Jim Ross, using chairs, cement blocks, and getting a little help from his assistant, Chief Morley. After beating Ross down for several minutes, Bischoff pinned him and won the match.
After debuting in the WWE, nobody expected that to happen, but it wouldn't be his only win. Kane counted himself out in a match against Bischoff, giving him another victory, but this time against a huge WWE Superstar.
12 Barry Horowitz
Barry Horowitz is one of the most well-known jobbers of all-time. The man turned losing into an art form in the WWE, as he fell victim to Superstar after Superstar on shows like Prime Time Wrestling, WWE Raw, and WWE Superstars. He may have gotten random wins on house shows against some unknown wrestlers, but when it came to TV time, Horowitz typically found himself lying flat on the mat.
In 1995, Horowitz was mocked and embarrassed by Skip, one half of The Bodydonnas tag team. After accepting a challenge, Horowitz shocked the WWE Universe by pinning Skip and winning the match. A few weeks later, a rematch was scheduled for SummerSlam. More than just winning a match, it was crazy to see Horowitz on a pay per view. Horowitz shocked the WWE world once again by defeating Skip at SummerSlam as well. The huge victory did not do much for Horowitz, as he quickly went back to his losing streak and was all but forgotten on WWE programming.
11 Earl Hebner
Earl Hebner is one of the great legendary referees. He has appeared in multiple WrestleMania main events and was a part of the WWE for some of the most iconic moments in history. While he could easily get between two wrestlers during an in-ring struggle, no one ever expected Hebner to compete in a match. That’s exactly what happened in 2001.
During the WCW "Invasion" angle, Hebner became involved when he started feuding with lead WCW referee, Nick Patrick. Instead of competing in some other type of contest, Hebner and Patrick were scheduled for a one-on-one match at the Invasion PPV. The match was messy and there wasn’t any type technical wrestling, but the crowd popped big time when Hebner hit a shoulder block and pinned Nick Patrick. Score one for the WWE referee crew!
10 The Coach
For some reason, the WWE always loves to include announcers and interviewers in physical storylines. This was certainly the case with Jonathan Coachman, AKA The Coach. He was fit, but clearly had no ring skills when it came to performing. He got his chance to showcase his "talents" during an episode of Monday Night Raw. In a Royal Rumble qualifying match, The Coach took on Jerry Lawler in a one-on-one battle. Lawler dominated the majority of the match, but it was The Coach who would have the last laugh.
This match took place on the same night where The Spirit Squad made their debut. The Squad decided to make Lawyer their first victim as they attacked him and helped The Coach secure a victory. The Coach was able to enter the Royal Rumble that year, but he was instantly eliminated by the Big Show, making the entire ordeal pretty pointless.
9 Vickie Guerrero
The former General Manager and wife of the late Eddie Guerrero was great on the mic, but no one ever expected her to compete in a WWE ring. This completely changed when the Miss WrestleMania Battle Royal was held at WrestleMania XXV. After "Santina Marella" won the match, Guerrero went on a crusade to win the title of “Miss WrestleMania” from him. She was finally granted a match on an episode of WWE Raw for the "prestigious" honor.
To the shock of the WWE fans, Guerrero defeated Santina and was declared the new “Miss WrestleMania.” The win would be short-lived as a rematch was scheduled for the Extreme Rules PPV. Vickie’s win streak would end at one as she competed and lost in a messy "Hog Pen Match".
Virgil stood by Ted DiBiase’s side for many years. The loyal manager was quiet and helpful as he distracted opponents and helped manage The Million Dollar Man’s fortunes. All good manager relationships must come to an end, but when Virgil and DiBiase broke up, he would not got quietly. Virgil decided to compete against his former boss and challenge him to a match at WrestleMania VII.
With Roddy Piper in his corner, Virgil represented the ultimate WrestleMania underdog. He was surprisingly good in the ring as the two performers provided an entertaining match. Virgil won the WrestleMania bout and officially kicked off a short singles career. The feud would continue into SummerSlam where Virgil would defeat his boss again and officially win The Million Dollar Championship. He would compete in next year’s WrestleMania as part of the winning team in a eight-man tag team match.
7 James Storm
One of TNA’s mainstays has always been James Storm. He has wrestled in the promotion for several years, winning big in both singles and tag team competition. Then Storm did the unexpected and was spotted at several NXT events. Many believed that Storm was just watching as a fan, but, a few weeks later, the TNA main event star was actually competing on NXT.
Storm wrestled in two televised matches for NXT. He earned a victory in both matches, but quietly left the WWE and returned to his roots in TNA. It was odd to see the TNA wrestler on WWE programming for such a brief period of time and pull out a couple of dominant victories. His quick return to TNA made the whole thing feel very surreal and it’s funny to say that James Storm has actually won a few WWE matches despite never having a contract with the company.
Celebrity wrestlers are typically hit or miss in the WWE and Jersey Shore star Snooki seemed like she was going to be a huge miss. The reality star got a chance to team up with John Morrison and Trish Stratus in a six-man tag team match at WrestleMania XXVII. No one was expecting much when Snooki entered the ring, but she put her gymnastic skills to good use and she was actually pretty decent for a first-timer.
Snooki not only wrestled at WrestleMania, but she earned the victory herself. She landed a splash on Michelle McCool and pinned her cleanly for the win. The win was surprising, but her ring skills were really impressive for a celebrity performer. The crowd watching the match was hesitant at first, but ended up cheering on the victory and the deserving win for Snooki.
5 Harvey Wippleman
The nerdy and feeble Harvey Wippleman was a second-rate manager in the WWE and an even worse wrestler when it came time to get physical. After disappearing from the WWE for several years, Wippleman’s big return wasn’t to manage the next great Superstar. It was an appearance in a drag costume which saw him compete for the Women's Championship.
Facing off against The Kat, Wippleman referred to himself as "Harvina" and would get involved in a messy and chaotic pool match. Wippleman ended up winning the match and was declared as the first-ever male WWE Woman’s Championship. Fans quickly figured out that it was Harvey and seemed a little confused as to why this former manager decided to go for the Women’s Championship. His reign was short-lived as Jacqueline dominated the male champ the next night and won the title back for the females.
4 Michael Cole
WWE announcer Michael Cole has been bullied, beat-up, and attacked by all types of WWE performers. He has no place competing in the WWE ring, but after a lengthy feud with Jerry Lawler, Cole would get an opportunity to compete at WrestleMania. With Jack Swagger in his corner, Cole felt confident as he was battling his former broadcast partner. The match was chaotic and became even crazier after special guest referee Stone Cold Steve Austin delivered stunners to everyone involved.
Despite getting beat up for several minutes, the official decision in the match was awarded to Michael Cole. With the victory, the long-time announcer can claim an undefeated record at WrestleMania. Rumors indicated a dream match between himself and The Undertaker but plans fell through when Taker was defeated...
3 Mr. Cena
John Cena’s feuds have gotten so personal that his father, Mr. Cena, would get involved. One of Mr. Cena’s first appearances was in a segment where Edge and Lita invaded his home before the 2006 SummerSlam event. While Mr. Cena gave some great story material for his son, no one ever expected him to compete in the ring.
That is exactly what happened during Cena’s feud with Randy Orton. Mr. Cena was forced into a match with Orton and Cena was handcuffed to the ring ropes, so he could not interfere. Mr. Cena suffered a whopping for several minutes and was eventually dropped flat with an RKO. Before Orton could pin Mr. Cena, John was able to undo the turnbuckle and get released from his cuffs. This caused Orton to retreat and gave Mr. Cena the technical win via count-out.
2 Stephen Amell
Playing a superhero on TV gave actor Stephen Amell plenty of experience to transition into a WWE ring. Amell began a feud with Stardust that eventually led to a tag team match at SummerSlam 2015. Teaming up with Neville, no one expected too much from Amell, but he definitely delivered. Amell was a large part of the action, including a huge dive off the top rope and he fell victim to several beat downs at the hands of Stardust and Wade Barrett.
Amell ended up scoring the victory at the second biggest PPV event of the year. It was a great moment and one of the better celebrity matches in WWE history. A singles match was supposed to take place a month later, but ended up getting canceled.
Shortly after Dusty Rhodes premiered in the WWE, we were introduced to one of his biggest fans – Sapphire. She would cheer on Dusty from outside the ring and then eventually accompany him to matches as his official valet. Sapphire clearly had no in-ring experience, but that didn’t stop Vince McMahon from booking her into a match.
At WrestleMania VI, Rhodes and Sapphire took on Macho Man Randy Savage and Queen Sherri in a mixed tag-team match. Rhodes handled most of the physical work, but it was Sapphire who ended up in the ring for the match ending. With a little help from Miss Elizabeth, Sapphire was able to pin Sherri and get the win for her team. It was a huge WrestleMania upset and helped establish Sapphire as a singles competitor for the remainder of 1990.
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