CM Punk's WWE Matches In Chicago Ranked From Worst To Best

After getting a brief first taste of a WWE World Championship the prior year, CM Punk found himself on the RAW roster's midcard as the calendar flipped from 2008 to 2009. Alongside his tag team championship partner Kofi Kingston (remember that?), the 'Second City Saint' entered a tournament in December to determine William Regal's next challenger for the Intercontinental Championship.

Punk bested Snitsky (in his final WWE match) and John Morrison on his way to the finale at Armageddon, where he secured the title shot by defeating the former World Champion, Rey Mysterio. The initial title match turned out to be a huge disappointment, though, as Regal conveniently got himself disqualified.

Thankfully, Stephanie McMahon was present to save the world as she always does, giving Punk a "last chance" rematch at the title in a No DQ match on the RAW before the Royal Rumble. An edition of RAW that just so happened to take place in Chi-town!

With the clear home-field advantage, Punk caught the champion by surprise early on with his series of kicks, strikes and submissions, before being the victim of a Layla distraction (Regal's valet at the time, wasn't 2009 a strange year...).

After surviving Regal's barrage of vicious knee strikes and headbutts, Punk valiantly came back and ended the physical tussle after hitting Regal with the GTS to win his first - and only - Intercontinental Championship.