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The Football League 100th Championship Challenge was a football match organised by the Football League and played to commemorate the 100th edition of the Football League First Division being completed. It was played between the winners of the competition's 100th edition, and the record winners of the competition at the time. It was held at the Stadium of Light on 18 May 1999, two days after the end of the Premier League season. The match was played between Sunderland, champions of the 1998–99 Football League First Division (the second-tier of English football at the time), and Liverpool, 18-time Football League champions (all first-tier titles).
Sunderland took an early lead through Allan Johnston's curling effort, but a penalty from Robbie Fowler and a close-range finish from Jamie Redknapp put Liverpool 2–1 in front. Sunderland brought the game back level via a Kevin Phillips header, but the Reds restored their lead within a minute when Paul Ince saw his deflected shot hit the back of the net. This proved to be the decisive goal as Liverpool won 3–2 to claim the glass trophy in front of a crowd of 18,111.
Sunderland manager Peter Reid expressed worry about the potential length of the injury suffered by their top scorer Kevin Phillips during the game, stating "We are just hoping it's a few torn fibres instead of a full-blown hamstring tear". Phillips was able to recover in time for the following season where he would end up winning the Premier League Golden Boot and the European Golden Shoe.