1. Portugal's runs at Euro 2000 and the 2006 World Cup. Euro 2000 was the first tournament I watched and it was a great team. 2006 is likely the best I'll ever see from them at a World Cup. One would assume it to be Euro 2016, but as I get older my emotional investment in sports continues to diminish, and coupled with the uninspiring way in which Portugal kept advancing, I didn't care about it nearly as much as I should have. No wins in a cupcake group, which was deflating. Then they begin the knockout stage with perhaps the most boring game I've ever seen against Croatia, a game so bad I would have turned off if I was a neutral, I nearly did anyway. I lost serious interest in the tournament from then on, even during the final I was watching half-halfheartedly, only briefly popping for Eder's goal. But thankfully, that experience provided me with the realization that even if the team I cheer for wins, it has no impact on my life, and I was unburdened from the irrational attachments that come with being a fan. I still have an interest, but the days of jovial enthusiasm are long gone. If they win, cool, if they lose, whatever. 2. -Euro 2004 final is by far the most crushing loss I've ever experienced in this sport. I was young and I cared too much. -Semi-final loss at 2006 WC sucked too but wasn't as bad as 2004. -Euro 2012 semi-final penalty shootout loss to Spain was a blow. -2002 WC was a disaster. The naivety and ignorance of being a kid led me to believe they were going to destroy everyone, and then in the first game they're down 3-0 after 30 minutes to the ****ing USA. lol. I think they were legitimate contenders too. -2014 WC was pathetic, a joke of a performance in all 3 games. I knew the team was **** though. My club affiliations lie with Benfica, my support for them isn't that involved but I have a couple I'll mention for them: -May 2013. They lost the league, Europa League, and domestic cup all in a span of a few weeks, and all to late winners. -2014 Europa League final, dominated Sevilla but lost on penalties.