Feature Photo: Shaun Botterill/Getty Images
Roberto Di Matteo was an understated player. Through Chelsea’s resurgence in the 1990s, he was at the heart of it. As classy a midfielder as the Premier League has seen, Di Matteo could do it all – he could pass, long and short, score and create goals and everything in between. He was quite brilliant.
Though he played in a team of superstars at the time and he was just one of them. But he was forced to bring an early end to his career at Chelsea – after six years and six major trophies, Di Matteo retired at the age of just 31 because of injury. It was a horrific triple leg fracture that initially sidelined him for 18 months and then forced him into a premature retirement. But he’d soon be back at Stamford Bridge.
Di Matteo took a short hiatus following the abrupt end to his playing career but returned as a manager in 2008. He was announced as Paul Ince’s replacement at English Football League side MK Dons. A move that shocked and surprised many, but ultimately worked out – the Italian guided the Dons to the Play-Off Final in his first and only season at the club, before being appointed at newly-relegated Championship side West Bromwich Albion.
Another impressive maiden campaign at his new club saw Di Matteo steer the Baggies to a 2nd-place finish, but he couldn’t cut it in the Premier League. He was sacked in February with the club two points off the bottom of the table, and Roy Hodgson came in and achieved an 11th-place finish. The 2011-12 season ended, and Chelsea gave Di Matteo a new lifeline in the form of the assistant manager role. Andre Villas-Boas was appointed ahead of the 2011-12 season, with Di Matteo as his new no.2.
That Chelsea side was phenomenal. Villas-Boas and Di Matteo inherited all of Petr Cech, John Terry, Ashley Cole, Frank Lampard, and Didier Drogba. That side was star-studded and expectations were high going into the new season. Claiming the Premier League title was the main focus for Villas-Boas after Chelsea finished 2nd to Manchester United the season before – many thought it was possible, but nobody could foretell the season that was coming Chelsea’s way.
A young and charismatic Villas-Boas arrived at Stamford Bridge from Porto. He’d achieved huge success there and left with a win percentage of over 84%, many tipping him to be the next “Special One.” But he lasted just 40 games in the job and became yet another up-and-coming manager to come under Roman Abramovich’s ruthless axe. Di Matteo was appointed caretaker manager until the end of the season.
It was a 1-0 defeat to Hodgson’s West Brom that saw Villas-Boas relieved of his duties in March 2012. The defeat left Chelsea three points outside the Champions League places, and their early dreams of a title-winning campaign were all but over. Di Matteo then had a big task on his hands. Nobody really expected the Italian to do anything but see Chelsea to a stable league finish, but he went above and beyond in the next two-and-a-half months.
Quite possibly the greatest managerial turnaround in modern Premier League history – bar, of course, Claudio Ranieri’s Leicester City achievement – Di Matteo went on to lift both the Champions League and FA Cup trophies for Chelsea, landing the job on a permanent deal ahead of the 2012-13 season. One of his first games as Chelsea’s caretaker manager was against Napoli in the Champions League Round of 16. Villas-Boas’ side lost the first leg in Naples 3-1 but progressed into the Quarter-Finals with a 4-1 win at Stamford Bridge. Di Matteo’s side then went on to beat Benfica and Barcelona, and Bayern Munich in the Final.
Four years on from their Moscow heartbreak at the hand of Manchester United, Chelsea lofted their first Champions League title and became the first London club to achieve that feat. That Final came two weeks after their FA Cup triumph over Liverpool and capped a momentous turnaround by Di Matteo’s side, who firmly put his name amongst some of the best managers in the world at that time.
In the space of a season, Di Matteo had gone from no.2, to achieving the greatest managerial feat in club football, and looked set to start a long and prosperous future with Chelsea. But as rapidly as he rose to stardom at the club, he fell right back down. Although Abramovich had brought the Champions League to Chelsea, he wanted more Premier League titles. The summer before the 2012-13 season, Di Matteo was funded over £80 million in transfer money, spending most of that on Eden Hazard and Oscar. Both were making waves in their respective leagues, and both would go on to have fine careers with Chelsea – Hazard’s obviously more so.
In terms of the Premier League, Chelsea were getting along nicely. They weren’t leading yet but they were well in the race. Di Matteo though missed out on the chance to secure his third and fourth trophies in the space of six months when he lost in both the FA Community Shield and the UEFA Super Cup finals. The club sacked Di Matteo in November 2012 after a 3-0 defeat to Juventus in the Champions League Group Stage, bringing an end to his eight-month Chelsea tenure. Rafa Benitez replaced him and would win the Europa League in his first half-season in charge.
After that, Di Matteo went on to an uninspiring seven-month spell with Schalke, before a forgetful twelve-match stint in charge of Aston Villa – winning just one game before being sacked in October 2016. Since then, Di Matteo has laid dormant. Within four years he’d gone from League One to Champions League glory. No manager has ever scaled as quickly as that before and none will do so for a long time.
Di Matteo achieved great things in such a short space of time at Chelsea and perhaps if he was given more time in his role, he could’ve been one of Europe’s top managers today.