5. vs. Liverpool
Competition FA Cup, Date 24th January 1999, Score 2-1 Ask any United fan who their most hated rival is and you'll be almost certain to get one answer Liverpool despite the Merseyside club's lack of success in the last two decades or so in comparison to United, as well as the likes of Arsenal, Chelsea and Manchester City. Regardless of either team's status, fixtures between the two are almost always heated and exciting affairs. This FA Cup fourth round tie was no different, and saw Michael Owen put Liverpool ahead after just two minutes. Despite creating a host of goalscoring opportunities, however, United just couldn't score an equaliser. It seemed like Liverpool, who United hadn't beaten in the competition since 1922, would walk away from Old Trafford as the victors, until Dwight Yorke finally managed to draw his side level with an 88th minute goal. Extra time then seemed likely, until Ole Gunnar Solskjaer scored in injury time to send Sir Alex's men into the fifth round, crushing the hopes of a Liverpool side who surely believed they'd done enough to ensure their own progression.