The match was played on 10 August 2008 between 2007–08 Premier League champions Manchester United and 2007–08 FA Cup winners Portsmouth as the "curtain-raiser" to the 2008–09 English football season.

[2] The match marked the 100th year since the first Charity Shield, also won by Manchester United after a replay in August 1908.

Manchester United won the game 3–1 on penalties, after the match finished 0–0 after 90 minutes; the Community Shield no longer plays extra time if the teams are level at the end of normal time.

[3][4] The match was the second meeting between the two teams in the space of two weeks, after they had played each other in a friendly in Nigeria on 27 July 2008.

It was also the first Community Shield since 1996 to feature a team from outside the big four of Manchester United, Chelsea, Arsenal and Liverpool.