Di Matteo only lasted 262 days in charge of Chelsea but during that brief time he enjoyed plenty of highs and lows.
Here Press Association Sport takes a look at some of them.
Champions League win
Di Matteo delivered the prize Roman Abramovich coveted the most following a memorable penalty shoot-out success over Bayern Munich in their own stadium. The Blues looked set for defeat until Didier Drogba headed a late equaliser and then slid home the winning spot-kick to spark wild celebrations.
FA Cup final
Di Matteo won his first trophy just months after being appointed when he led the Blues to a 2-1 victory over Liverpool at Wembley. Ramires and Drogba fired them ahead before Andy Carroll pulled back a goals for the Reds.
Masterminding Barça demise
Arguably Di Matteo's finest moment as a tactician came in plotting the downfall of Pep Guardiola's Barcelona in last season's Champions League semi-final. After a hard-earned 1-0 home win in the first leg the Blues progressed following a barely believable return match at the Nou Camp. They looked dead and buried when Barça scored twice and captain John Terry saw red. But Ramires pulled a goal back before half-time and after Lionel Messi missed a penalty Fernando Torres sealed a famous night with his breakaway goal in the final moments.
Start to season
Chelsea were flying high at the top of the Barclays Premier League table at the start of the season, dropping just two points in their opening eight games. New signings Eden Hazard and Oscar were revelling in their new surroundings in a potent trident of playmakers led by Juan Mata. Torres was even scoring, including a memorable strike after a one-two with Hazard against Newcastle.
Super Cup thumping
The first signpost towards Chelsea's ills in Europe this season came with a thumping 4-1 Super Cup defeat to Atletico Madrid in August. Madrid striker Radamel Falcao struck a hat-trick to immediately put himself on Chelsea's transfer radar.
Few would have expected Di Matteo to be sacked following the 3-0 reverse - Chelsea's biggest Champions League group stage defeat - but it did leave the club on the brink of elimination from the competition he had won to convince Abramovich to retain him last summer.
A spectacular start to the season began to hit the skids during a stormy home 3-2 defeat to Manchester United last month. Aside from being the Blues' first league defeat the match was played out on a backdrop of ill feeling after the hosts had two men sent off by referee Mark Clattenburg. The club then alleged Clattenburg used inappropriate language towards John Obi Mikel, claims the official denies.