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Toughest Sports Loss You've Ever Suffered as a Fan ?
#13
Kentucky Basketball-- all of these are tied for different reasons (including sentimental ones):
15  - Wisconsin - Final Four
97 - Arizona - NCAA Final
92 - Duke - Elite Eight
14 - UConn - Final

Kentucky Football--
97 - Florida - In hindsight, I don't even know why I was excited
03 - Arkansas - 8 OT game
03 - Florida - went into the 4th with a 21 point lead
07 - Tennessee - one of many squandered to the puke-orange Vols


NBA --
03 - Kings vs. Lakers -- loved watching the Kings move the ball and play so loose but came to realize just how fixed the NBA was and haven't looked at the game in the same light since. The Donaghy scandal proves that this isn't some tinfoil hat theory. This one is probably one of the toughest in a "life just isn't fair and never will be" sense.

NFL --
19 - Texans vs. Chiefs -- Houston builds a 24-0 lead before falling 51-31.

MLB --
95 - Reds vs. Braves -- I knew that this was the end and that it'd be a long time before they were good again.


High School --
99 - Tilghman vs. Scott County -- not quite high school basketball's definition of righteous indignation, but it's one that most of us collectively witnessed and it probably doesn't need tons of explanation. This is the worst that I've felt for a group of kids after a Sweet 16 game.

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