WWE has been the world's top wrestling promotion for decades, and it has managed to stay on top because the company has consistently signed and developed top tier talent. CM Punk joined WWE back in 2006, and during his 8-year tenure with the company, he became a 3-time world champion.
He won a bunch of other titles along the way too, and the fans loved him because of his amazing promo skills, but it also helped that he was good in the ring. Punk retired in 2014, and at that point he had hundreds of matches under his belt, and while some of those matches were bad, some of those matches were truly the worst.
10 Vs. The Undertaker (Breaking Point 2009)
Punk was undoubtedly the top heel in 2009, and when he was done feuding with Jeff Hardy, he moved on to face The Undertaker. They may have eventually had a good match at WrestleMania 29, but their match at Breaking Point in 2009 is hands down one of the worst World Heavyweight Championship matches of the last 20 years.
This Submission match was their first one-on-one meeting, and it turned out to be a total let down. The match itself was incredibly clunky, and it ended similar to the infamous Montreal Screwjob, as the referee rang the bell while 'Taker was in Punk's Anaconda Vice, but he never actually tapped.
9 Vs. Triple H (Night Of Champions 2011)
Wrestling fans are well aware of the fact that Punk doesn't like Triple H, and part of that animosity definitely came from their No Holds Barred match at Night Of Champions in 2011. Prior to this match, Punk and Triple H delivered a number of great promos, and it appeared as though they were going to put on a clinic.
The actual match had its moments, but it was nowhere near the classic it was expected to be. Triple H ended up winning, which brought an abrupt end to Punk's hot streak, and it would have meant more if The Miz, R-Truth and Kevin Nash hadn't all interfered in the match.
8 Vs. Umaga (Extreme Rules 2009)
After losing the World Heavyweight Championship, Punk was sent to SmackDown, where he was expected to shine, but his first feud on the brand ended up being with Umaga. This led to a match at Judgement Day, and Umaga continued to target Punk after picking up the win.
This led to their Samoan Strap match at Extreme Rules in 2009. Strap matches tend to get boring very quickly because they limit the superstars' move sets, and this happened during their match as well, which is unfortunate because it turned out to be Umaga's final match.
7 Vs. JBL (SummerSlam 2008)
Punk won the Money on the Bank contract at WrestleMania XXIV, and he went on to successfully cash it in on Edge on Raw in the summer of 2008. This was Punk's first World Heavyweight Championship, and thanks to horrible booking, it was a terrible reign.
By the time SummerSlam came around, Punk was in a feud with JBL, and although they were perfect rivals from a storyline standpoint, they never had any real in-ring chemistry. Punk was the babyface in this feud, and although he picked up a clean win, the match was a lackluster affair that did virtually nothing to elevate Punk's status.
6 Vs. Johnny Nitro (Vengeance 2007)
Vengeance: Night of Champions saw every WWE championship up grabs, including the then vacant ECW Championship, and that match pitted Punk against John Morrison (then known as Johnny Nitro). Punk was originally booked to face Chris Benoit, but when he failed to show up, Nitro was picked to replace him.
Many fans believed that Punk was finally going to win the title, but it was Nitro who walked away as champion, despite the fact that he was still a newcomer to ECW. Their match was incredibly dull, and this wouldn't have been the case if Punk had taken on Benoit as planned.
5 Vs. Ryback & Paul Heyman (Hell In A Cell 2013)
Punk is arguably the best client that Paul Heyman has ever had, which is why their feud in the summer of 2013 was so good. But the feud lost steam when Ryback came in to replace Brock Lesnar, who decided to go on a small hiatus. Punk and Ryback had some good matches, but their bout at Hell in a Cell left many disappointed.
This was actually a triple threat match that included Heyman, but he spent the majority of the match hiding from Punk on top of the cell, and he wasn't even involved in the finish. The match itself lasted for less than 15 minutes, and Ryback got virtually no offense in, which would have been fine if the bout wasn't boring.
4 Vs. Matt Striker (ECW Taping 2007)
Matt Striker competed in WWE for three years, but he spent the majority of that time as a jobber, and for some reason WWE picked him to hand Punk his second loss with the company. This happened at an ECW taping in 2007, and it will forever be a stain on Punk's WWE carrier.
This win made absolutely no sense because leading up to it, Punk had been on an impressive winning streak, which included several wins over Striker, who at the time had a dismal teacher's gimmick.
3 Vs. Big Show (Night Of Champions 2010)
Big Show has had a very long career, and he has had his fair share of embarrassing moments, but his match with CM Punk at Night of Champions was not one of them. Punk and his Straight Edge Society lost to Big Show at SummerSlam despite it being a 3-on-1 handicap match.
Punk went on to cut a great promo in his hometown where he claimed that he could beat the massive athlete on his own, and it looked as though he was going to pull it off, but when they met at the pay-per-view, Punk got in no offense, and the bout was nothing more than a 4-minute squash match.
2 Vs. Batista (Great American Bash 2008)
Batista had some amazing matches over the course of his career, but his match with Punk at the 2008 edition of The Great American Bash was not one of them. The mini-feud between the two was completely one-sided in Batista's favor, and the biggest storyline associated with the match was the controversy surrounding Kane, instead of the actual title.
The match saw Punk get in more offense than expected, but Batista was still dominant, and it ended in a double disqualification because of Kane's interference. Fans loath these types of finishes, and it did nothing but add to Punk's disastrous first World Heavyweight Championship reign.
1 Vs. Big Daddy V (No Mercy 2007)
Punk won the ECW Championship in 2007, and his feud with John Morrison was supposed to continue, but when Morrison got suspended for violating WWE's Wellness Policy, a replacement for his title defense at No Mercy needed to be found.
That replacement ended up being Big Daddy V, who had just been drafted to ECW from Raw, and their match turned out to be a total train wreck. There was virtually no build-up to the match, and Big Daddy V was barely able to keep up with Punk, who tried his best to carry him through the two-minute bout.