Chelsea took the lead just 42 seconds into the match, with Italian midfielder Roberto Di Matteo receiving the ball and firing it into the goal off the crossbar from 25 yards to record what was at the time the quickest ever goal in a Wembley FA Cup final, breaking Jackie Milburn's 42-year record (Louis Saha broke this record 12 years later in the 2009 final after just 25 seconds, ironically against Chelsea, though Chelsea won the match against Everton 2-1). Middlesbrough's prolific striker Fabrizio Ravanelli limped off after 21 minutes, further diminishing his side's chances of victory. Late in the first half Gianluca Festa put the ball in the net for Middlesbrough, but the goal was ruled out for offside. In a largely disappointing match, in which Chelsea were generally in control, Chelsea eventually added a second goal seven minutes from full-time with Eddie Newton steering the ball into the net from Gianfranco Zola's clever flick to seal a 2–0 win.
Following a poor quality first half in which few chances were created, the match was brighter in the second, with Chelsea generally having the better of the play. George Weah missed several chances and Dennis Wise had a goal disallowed for offside, while Villa's Gareth Southgate headed wide. On 73 minutes, Roberto Di Matteo scored what proved to be the winning goal, capitalising on an error from Villa goalkeeper David James to put the ball in the net from close range. James came roaring off his line to deal with Zola's free-kick from the left, he fumbled the ball against Gareth Southgate's chest with Di Matteo blasting the rebound into the roof of the net. Villa could not get back in the match, their best chance falling to Benito Carbone, but his tame shot did not test Ed de Goey in goal.