There's definitely a lot of painful memories in this thread, and I remember all of them going back to the late 1970s. For me, though, the most painful three weeks I have ever been through as a young Dallas Cowboys fan was the end of the 1983 season.
The team arrives at game #15 against the hated Washington Commanders who were the defending champs. The Cowboys were the only team to beat the Skins in the 1982 strike shortened year, and thus prevented a cheap undefeated season. The Cowboys had also beaten the Skins on the Monday Night opener with an miraculous 20 point halftime deficit comeback to win 31-30.
The Cowboys would go on to a 7-0 lead, and were 12-2 going in to that game against the Skins. Not only that, but Dallas should have been 14-0 at that point as they gave away a 2 point loss to the Raiders and a 1 point loss to the Chargers (the first time SD had ever beaten Dallas btw). Just one more FG in each game or one more defensive stop in each and we are 14-0.
Before I get to the last few games I must point out that I lived in California at the time, and was surrounded by 49ers, Raiders and Rams fans who all collectively hated Dallas more than any other team. I had lost my lunch money in a bet over the Raiders game, and had to eat all their trash talk, but I still had a lot of confidence in Dallas because they were the strongest looking team in the league headed into week 15.
And then we got blown out by the Commanders 31-10. Just looked like crap the whole game. This sucked, I was extremely mad on that one. I got in arguments at school (8th grade), and nearly got into a fist fight over it. The PE teacher had to step in and warn the both of us to knock it off or go to the office.
Still, I shook that off as just a bad game after a few days. We were still 12-3, and the Skins were defending champs... and then we got blown out 42-17 by San Francisco. I was so humiliated, and so stressed by the prospect of facing a huge mass of 49ers fans all just ready to feed me crow that I faked being sick so I could skip Monday. Of course, this only slightly worked as they were ready and waiting on Tuesday. That was one of the hardest 4 days of school I think I have ever been through, and it had nothing to do with tests or anything scholastic.
Oh well, 12-4 is still a really strong record even if we had to settle for the wildcard. We would face the lowly Los Angeles Rams in the wildcard game. Surely we still had the nuts to beat a weak 9-7 Rams teams that earlier in the year we would have stomped by three or four TDs if we had played them. And then the Cowboys lost to a far inferior team 24-17. I was completely crushed as I had just been through the worst collapse in team history in my opinion. Three straight losses after starting 12-2 and should have been 14-0.
To make matters worse my best friend was a Rams fans and so I once again faked being sick to skip a school day of eating yet more crow. It was also not lost on me that I lived in California and Dallas went 0-4 against all 4 California teams at the time. Just brutal for a 13 year old kid to have to go through.