#3 Ric Flair (TLC Match vs. Edge on WWE RAW 16/1/2006)
At 56-years-old at the time, Ric Flair's performance in his TLC Match against WWE Champion Edge was remarkable. He put himself through a tremendous amount of pain, putting the Rated-R Superstar over as the biggest heel in the company. This came in the aftermath of Edge's Money in the Bank cash-in on John Cena and subsequent celebration with Lita.
With the match taking place in Flair's hometown of Charlotte, North Carolina, and it being the blow-off to a personal feud, there seemed to be a genuine belief that the Nature Boy would pull it off and win his 17th world title. TLC was Edge's specialty, stacking the odds further against the veteran.
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The match was brutal and inventive, featuring high drama, dangerous spots, and of course, some blood. Lita got involved as well, eventually turning the tide in Edge's favor. Flair put up an incredible fight, especially considering it was TLC, but it was not enough to bring home the belt.
While this was one of the many TLC matches that Edge won, the two-time WWE Hall of Famer did well to put his younger opponent over. However, Ric Flair was not the oldest Superstar to ever partake in a TLC match.