History of Chelsea F.C. gave Chelsea a 2–1 victory over Everton in the FA Cup final at Wembley on 30 May, the club's second FA Cup triumph in three years. Former Milan coach Carlo Ancelotti was confirmed as Hiddink's successor on 1 June 2009. He started his career by winning the World Football Challenge, played in the United States. In Ancelotti's first competitive match, Chelsea met Manchester United in the Community Shield. The game ended in a 2–2 draw, with Chelsea winning 4–1 on penalties to take the trophy, the club's first victory in a shoot-out since beating Ipswich Town in the League Cup
1991 FA Charity Shield Chelsea – in the entire campaign. This was the club's eleventh Charity Shield appearance; Arsenal won seven previous shields (1930, 1931, 1933, 1934, 1938, 1948, 1953) and lost four (1935, 1936, 1979, 1989) previously. Tottenham Hotspur qualified as holders of the FA Cup, beating Nottingham Forest 2–1 in the 1991 FA Cup Final. They appeared in five previous shields, winning four outright (1921, 1951, 1961, 1962), sharing two (1967, 1981) and losing two (1920, 1982). The last meeting between both teams was in the FA Cup; Tottenham Hotspur won 3–1 in the semi-final at Wembley Stadium. Tottenham were the only