Year fired: 2012
Previous season: Won Champions League and FA Cup
Di Matteo became Chelsea's interim coach in the middle of a shitstorm. Under André Villas-Boas, the squad had just lost 3-1 to Napoli in the first leg of a Champions League matchup, and to West Bromwich Albion in the Premier League, placing the team three points behind fourth-place Arsenal.
Somehow Di Matteo switched up the juju, beginning with a 4-1 victory over Napoli in the second leg to advance to the quarter-finals. Improbability didn't stop Chelsea as they took down mighty Barcelona and Bayern Munich to become the champions of Europe. Di Matteo was appointed full-time manager in the off-season, but it didn't last long. He was fired halfway through the 2012-2013 season.