In 2006 I was disappointed, but at the time I really thought they would build on that momentum in 2007. In some I felt the disappointment more in 2007 when it did not become 2006 part 2. 2009 -- was a disappointment - but the Yankees were pretty dominant that year, I might have felt game 163 more the previous year. 2010 -- I saw a regular season game the last week of the season and Thome and Mauer could barely hobble to first base and Justin was out - so while they had a pretty good season by that point they were pretty beat up and in retrospect signs of things to come in 2011. 2019 - I did not think they were as good as their record. A lot of it was padded by playing some really bad teams in April and September and they were pretty mediocre the middle of the season. I did not necessarily expect them to advance, but I did expect them to play better than they did and at least be competitive. I think this year the play-off losing streak weighed on me a bit more. The '98 Vikings was probably my biggest disappointment. I was a little too young to be invested in the early super bowl losses, and if I remember correctly people were prepared for them to lose number 4. It is crazy to think they have not even made to the big game in over 40 years when they went 4 times in my first 8 years of life. The 98 game might have crushed something in my soul, because while I have been disappointed by other Viking losses (see, Favre, Brett), I am not sure I have ever felt quite as kicked in the gut since then. My high school football team mid-80's --- so close to making it to State at a time where it was harder to even make it to the play-offs for high school football. I suppose the most crushing losses to me were high school related.