Which Grey Cup Loss was Most Difficult?

[Jesse]

2024 had the least emotional impact for me (other than recency).

2022 hurt the most because I was there.

But 2023 was the one that got away. No reason we should have lost that game.

[BLUEBOMBER]

They were all equally as upsetting... arguably the BB should have won all the games.

[peg_city]

Not enough choices. I still haven't gotten over losing in 1965.  However, of the choices given I pick 2022.

2001 was worse than either of these three (for me).

[blue_gold_84]

2001 was worse than either of these three (for me).

Ditto. That inexcusable loss still chaps my hide to this day.