I think exiting to Manchester United in 2009 is what stings the most. Ibra screwed up!
I was wondering what you have deemed the most painful moment watching Inter Milan in the past.
My most painful moment watching Inter came on the 5th of May 2002 - when we lost the league on the last game of season vs Lazio .
What's yours?
Manchester United 2 - 0 Inter (UCL 2008/2009 - 1/8 Finals).
Oh well, I hadn't noticed this thread.
(1) May 5, 2002: (Lazio 4-2 Inter)
(2) 2003: Champions League semi-final against Milan (knocked out on away goal rule)
(3) Ronaldo's departure
(4) 2001: Inter 0-6 Milan
..... There are many more for sure but the above ones are in a totally different level.