Roberto Di Matteo

The playing career of Chelsea midfielder Roberto Di Matteo was curtailed prematurely by injury in 2002 and, while running restaurant businesses on the side, he pursued coaching qualifications alongside fellow 1997 FA Cup final-winning goalscorer, Eddie Newton.

With Newton as assistant Di Matteo took over as manager of MK Dons, then earned promotion with West Bromwich Albion, earning rave reviews for the fluid, attacking football his sides played. It was a balanced pairing: Di Matteo cool, thoughtful, unflappable; Newton approachable, energetic, hard-working. When Andre Villas-Boas was appointed Albion’s head coach in summer 2011 Di Matteo was out of work and returned to the Bridge as assistant, stepping up as interim first team coach when things went awry for the Portuguese.

He turned again to Newton to join the existing staff and on the back of immense goodwill from fans a fairy tale unfolded for the popular ex-Blues. The Italian’s focus on cups ultimately proved successful and his rehabilitation – Terry, Lampard and Drogba – even shrewder.

The stunning overturn of a 1-3 deficit to Napoli was one the great nights at the Bridge, pragmatically achieved with the ‘old guard’ reinstated. An old foe, Liverpool, were beaten in the 2012 FA Cup final, but it was a sensational sequence in the Champions League that captured the imagination of world football. Defensive organisation – not always the Italian’s strength in the league campaign – was to the fore as the Blues recorded a spine-tingling 2-2 semi-final draw at Camp Nou to progress to the final against Bayern Munich on their home soil. In an astute piece of motivational management the night before the showdown, Di Matteo showed the squad touching video messages of support recorded by their families.

After Drogba’s penalty defeated the Germans the players flung the first Chelsea manager to win the Champions League in the air in celebration. In retrospect the Italian, like Drogba, should perhaps have left on a high, for his permanent appointment did not run the two years intended. A 0-3 defeat at Juventus in November 2012 epitomised the Blues’ poor defence of the European title and a run of two wins in eight Premier League outings brought an end to a sometimes dazzling eight-month reign.