Number 19: Tables, Ladders, and Chairs Match for the WWE Championship Edge (c) defeated Ric Flair January 16, 2006
As far as Raw's milestone matches go, you'd be hard-pressed to find many that were more spectacular – and emotional – than Ric Flair vs. Edge.
The first TLC Match for the WWE Title began routinely enough as the 16-time World Champion belted Edge with a flurry of stinging chops, but The Rated-R Superstar wasted no time using the ladder as a weapon. A veteran of 10 different kinds of Ladder Matches, Edge knew exactly what he was doing as he sandwiched Flair in the ladder and unloaded with a steel chair. Flair suffered number of brutal shots in the nearly 15-minute bout, including a flying crossbody from Edge off the ladder that drove him through a table. The agony was palpable as the bludgeoned "Nature Boy" shouted out in pain as his daughter pleaded, "Dad, please get up!" from the front row. Incredibly, Slick Ric rallied back and looked like he would've won the match if not for Lita's persistent meddling, which bought Edge enough time to knock Flair off the top of the ladder and retain his WWE Championship.