Without a doubt...

Jeff Lacy - Joe Calzaghe.

It should have been a great fight. Because I KNEW that Calzaghe would engage with Lacy on the inside and I knew that would be a mistake. I literally spent DAYS going over that fight. I downloaded a ton of Calzaghe fights. Downloaded Lacy's career (even though I've seen most of it). Went over it a lot.

First round came around. Bam, inside. Calzaghe got the better but I knew Lacy would make him pay. Instead he looked more worried about the positioning of his trunks. Had a bunch of friends over. About round nine, I just died. After, Cotto fight I watched, but I couldn't pay attention. Bout as down in the dumps as I've ever been as a sports fan. Either that or when the Giants lost the World Series in 02. I don't think so though.

That was definitely the biggest disappointment of my boxing watching career. Most of the mega fights I've only seen in hindsight, and the other ones I can usually predict how the fight is going to go even if I don't pick the winner right. But that was my favorite fighter getting absolutely destroyed by my least favorite fighter and that sucked....

Also every Tyson fight I have ever seen live has been fairly depressing because I knew he was once a great fighter.