35 years of hurt...your top five low points

In addition to all of the events mentioned so far, of which going 2 down to Gillingham was unquestionably the worst, from a purely footballing point of view I would add a 3-0 midweek defeat to Reading at Elm Park, either earlier that same season, or possibly the season before, and a 0-0 draw at home to Bristol Rovers (the week before the official York City nadir), when they had 5 or 6 teenagers in the side due to an injury crisis. Without doubt the two worst City performances I've witnessed in 40 plus years of supporting the club. Wycombe Wanderers away, when Royle fielded 4 centre halves across the back and 4 converted full backs in midfield, with a 108 year old Peter Beardsley up front, pushed them pretty fucking close mind (we lost 1-0 without having a shot). Happy days.
 

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