Chelsea have taken part in ten Charity Shield or Community Shield matches in the Premier League era alone, however their win percentage isn’t the greatest!
(table of wins goes here)
Chelsea Community Shield / Charity Shield Wins
2009 Community Shield Win
In as FA Cup winners to face league champions Manchester United, Carlo Ancelotti’s team put aside the disappointment of seeing Nani score a stoppage-time equaliser at Wembley in 2009 to ultimately win out on penalties and land the Community Shield for a fourth time.
2005 Community Shield Win
Playing as the 2005 Premier League champions against cup winners Arsenal, a Chelsea side led by Jose Mourinho proved too strong for the Gunners in Cardiff as goals from Didier Drogba were enough for the Blues to claim a 2-1 win.
2000 Charity Shield Win
Gianluca Vialli’s FA Cup winners qualified to play title winners Manchester United at Wembley in 2000 with 65,000 in attendance. Goals from Jimmy Floyd Hasselbaink and Mario Melchiot were enough on this occasion to seal Chelsea their first Charity Shield in 45 years.
1955 Charity Shield Win
Newcastle United’s great run of FA Cup wins in the 50’s led to them taking part in the 1955 Charity Shield, but they had to face league champions Chelsea at Stamford Bridge and ultimately the Blues were too strong, coming out 3-0 winners in the end.
Near Misses
Chelsea have a rather unfortunate record in the Community Shield during the Premier League era, losing seven times at either Wembley or Cardiff. Their runners-up spots came in 2006, 2007, 2010, 2012, 2015, 2017 and 2018.