I never answered these either:
Whats your most depressing sporting event that you witnessed live?
My first and only Jets game in person. A boring, crappy, horribly officiated game against the Packers 2 years ago, where neither team scored a touchdown and the Jets lost like 9-0.
Most depressing or crushing loss in a sport you don't usually care about?
USA/Canada Gold Medal game in the 2010 Olympics. Almost made me into a hockey fan.
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SephirothG, channeling awesomeness from Mershiness.
The Resurrection