Skopje 1999 was the worst for me. Dreadful day when it looked like we'd be on a runway in Rimini while the game was being played but just made it by kickoff but really for the abject performance and the late goal. They were a poor side missing 9 players and we threw away qualification.
Other notables - Roy Keane as sweeper to hold mighty Iceland 0-0 at Lansdowne in 96. Norway 0-0 in 85. Losing at home to austria in 95 just after the debacle in Liechtenstein.
Israel away will be up there too. Playing Poland off the park for 75 minutes leading 3-1 and then gifting them 2 goals in 91 was a bad one too that ultimately cost us a trip to Sweden.
On the football field I don't think we disgraced ourselves at any of the major finals. Could have done better and empty feelings particularly 94 but Holland twice, Italy and Spain are major footballing sides.
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