I'm only 31, so most of the really bad moments were before my time, but in no particular order:
- Randy Moss game.
- Aikman's retirement/Irvin's career ending injury.
- Losing to the Texans in 2002.
- Campo years collectively. Seemed like every time I watched a game or checked the FOX ticker at the bottom of the screen back then, it was an L.
- Emmitt being cut and signing with the Cardinals.
- Botched Romo fumble. Still don't think I'm over it to this day.
- Parcells moving on.
- Losing to the Giants in the '07 Divisional.
- Brett Favre 34-3 rout my Freshman year of college back in '09.
- Imploding against the Ravens in the Texas Stadium finale.
- 2009 Draft.
- Starting 1-7 in 2010, which ultimately led to the hiring of Garrett.
- 3 straight 8-8 seasons, with each of our division rivals sending us on our way in de-facto championship games the last week of the season.
- The loss against the Broncos in the famous Romo/Payton Manning duel.
- Dez catch/Demarco Murray fumble.
- Cliff Avril sack on Romo in the preseason.
- Panthers Thanksgiving Day debacle.
- Aaron Rodgers to Jared Cook on 3rd and 20.
- 42-17 loss against the Broncos in 2017.
- Allowing almost 300 yards rushing to Gurley and CJ Anderson.
- Losing to a moribund Jets team in 2019, and our defense being clowned by Darnold post-game.
- 2021 WC game against SF.