On 15 January 1959, Southern League Worcester City staged one of the biggest upsets in FA Cup history by beating Liverpool 2-1 at St. George's Lane in the third round.
At the time, Liverpool were in second place in the Second Division table, three levels above non-League strugglers Worcester City. City, however, had announced their intentions by beating Fourth Division side Millwall 5-2 in the previous round. Originally scheduled to be played on a Saturday, the frozen pitch at St. George's Lane forced a postponement to midweek. The delay heightened the anticipation for the supporters, who set a club record attendance at the time of 15,000 for the Liverpool match.
Those supporters were delighted when City's Tommy Skuse scored the opening goal in the ninth minute. He outraced the Liverpool defenders to catch a deflected ball and tucked it home to put City up 1-0, a lead they held through the break. Late in the second half, City appeared to seal their victory when Liverpool center-half Dick White botched a clearance in the 81st minute by lobbing the ball over his own keeper and into the net.
The Merseysiders pulled one back a minute later after converting a controversial penalty, but it wasn't enough and Liverpool were eliminated. City advanced to the fourth round, where they lost at home to Sheffield United, 2-0.
The loss remains Liverpool's worst Cup defeat, but not their most recent, as second division Reading dumped them out of the competition on 13 January 2009.