Coventry City 2-1 Chelsea 1999
While they were not at their imperious best by the 1998-1999 season, the Blues were definitely a club on the rise having finished 4th in the previous season. Post the sacking of Ruud Gullit in February 1998, the club had appointed Gianluca Vialli as a player-manager and the former Italian international was expected to ring the right changes at the club to ensure that they claim their first league title since the 1954-55 season.
However, the London club’s aspirations were dealt a blow by Coventry who beat them courtesy of early goals from Darren Huckerby (10th minute) and Dion Dublin (16th minute). Though Guus Poyet restored the single goal difference in the 37th minute, the London club was not able to capitalise on the momentum and suffered a shock defeat at the hands of Coventry, a side which eventually finished 15th in the season.