re: What's the most devastating regular season loss for each football program?

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Kentucky - 1950 Tennessee? Bluegrass Miracle?

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#1 That game in the late 70's or early 80's in CWS when they lost to Bear Bryant very late in the game with a 2 TD lead.

#1a The current Florida skid. While not a single game it is collectively a heavy burden that needs to be lifted.