5. Jeff Gordon Matt Kenseth 2008
It’s early in the 2008 Cup Series season and while wins ultimately pay the most points at the end of the day, every single position matters. In fact, with the implementation of "win and you're in" not happening for almost another decade, every single position on the track was critical in gaining a spot in that year's playoffs.
With that being said, Matt Kenseth and Jeff Gordon were battling for position in the final laps when the unthinkable happened. Gordon accidentally sailed his car into the turn on the high side and hit Kenseth’s quarter panel as a result. This caused Kenseth to spin right in front of Gordon, which forced the four-time champion to veer out of the way.
Unfortunately for Gordon, he ended up overcorrecting his car, getting loose, and launching himself into the inside wall. Keep in mind that while parts of the outside wall were protected with Styrofoam to minimize the impact of an accident, the inside walls weren’t. This meant that Gordon went head-on into the inside retaining wall in what he even describes as one of the worst wrecks of his career.