The managerial career of Roberto Di Matteo, particularly with regards to his time at Chelsea, might be one of the most fascinating in the history of football. He arrived at the club as an assistant to André Villas-Boas, but when the Portuguese manager was sacked the club turned to the Italian to take over for the rest of the season. He won both the FA Cup and the Champions League, was named the club’s permanent manager on a full-time basis and then was sacked months later. In terms of time spent in position compared to trophies won, he might be the best manager Chelsea have ever had, whilst also being one of the poorest.
Roberto Di Matteo’s Honours as Chelsea Manager
| Season | League Titles | Domestic Cups | European/International Cups |
|---|---|---|---|
| 2011/12 | – | FA Cup | Champions League |
Di Matteo the Player
It is fair to say that the fascinating nature of Roberto Di Matteo even extends to his youth, given the fact that he was born in the town of Schaffhausen in Switzerland on the 29th of May 1970. That means that he is, of course, Swiss by birth, although the fact that he was born to Italian parents from the region of Abruzzo means that he is Italian in heritage. He grew up in Switzerland, though, and when he began playing it was for the local side in Schaffhausen. In 1991, after scoring two goals in 50 league games, he moved to FC Zürich and scored six times in 34 league games, earning him a move to Aarau.
That moved proved to be a wise one and Di Matteo had won the Swiss Nationalliga A within a few months of his of arrival there, scoring one goal in his 33 league games for the club. When his contract was up, his spiritual home came calling in the form of Lazio, where he signed in 1993. He quickly became the starting 11 for the Italian side, with both Dino Zoff and Zdeněk Zeman turning to him during his three seasons there. This led to him being called up to the Italian national team, making his debut under Arrigo Saachi in 1994 when he came on as a substitute in a game that Italy actually lost to Croatia.
Playing for Chelsea
Between 1994 and 1998 he earned 34 caps for his nation side, scoring two goals. In the middle of that period, Di Matteo was signed by Chelsea, scoring a goal on his debut, which ended up being the winner against Middlesbrough. Both his passing ability and his long-range shooting saw him become a fan favourite, as well as part of the reason why the London club were revitalised in the latter part of the 1990s. He scored nine goals in the 1996-1997 season, which helped the Blues finish sixth in the league. More importantly, he scored the opening goal of the FA Cup final, again against Middlesbrough, after just 42 seconds.
The Blues held on to win the final 2-0, with the goal scored by the Italian being the quickest in FA Cup final history until it was out-done by Louis Saha for Everton in 2009. Ten goals and several assists came the following season, helping Chelsea to win both the League Cup and the Cup Winners’ Cup. The League Cup final saw the Blues come up against Middlesbrough again, with Di Matteo once more proving his worth by scoring the second goal of the game in a 2-0 win. Chelsea finished third in the Premier League, with Di Matteo part of a strong midfield unit that included Gus Poyet, Dennis Wise and Dan Petrescu.
His 1999-2000 season was marred by injury, but he returned to the Chelsea team in time to not only make the FA Cup final but also score the only goal of the game, allowing the Blues to win the trophy at the expense of Aston Villa. As the 2000-2001 season got underway, Di Matteo was injured in a match between Chelsea and St. Gallen in the UEFA Cup, suffering a triple leg fracture. Though he hoped to return to the team, he eventually gave up any hope of being able to play again in the February of 2002, retiring as a 31-year-old who had scored 26 goals across 175 appearances during his six year spell at Stamford Bridge.
Roberto Di Matteo’s Honours as Chelsea Player
| Season | League Titles | Domestic Cups | European/International Cups |
|---|---|---|---|
| 1996/97 | – | FA Cup | – |
| 1997/98 | – | League Cup | Cup Winners’ Cup |
| 1998/99 | – | – | Super Cup |
| 1999/00 | – | FA Cup | – |
| 2000/01 | – | Charity Shield | – |
Getting Into Management
On the second of July 2008, Paul Ince decided to leave his role as the Milton Keynes Dons manager in order to become the boss at Blackburn Rovers. The club turned to Di Matteo as the new manager, with both parties considering themselves to be ‘young, ambitious and hungry to succeed’. He persuaded his formed Chelsea teammate Tore André Flo to come out of retirement and sign for the club until the end of the season, leading them to a third place finish in League One. That allowed them to qualify for the play-offs, with Flo missing the decisive penalty in a sudden death scenario in the semi-final match against Scunthorpe United.
In the June of the following year, Di Matteo took over as the boss at West Bromwich Albion. He was brought in after the Baggies had been relegated from the Premier League, with former manager Tony Mowbray taking the Celtic job. He got them automatic promotion back into the top-flight behind Newcastle United, with the first game being at Stamford Bridge. He was given a warm welcome by supporters, which was even warmer when the home side won 6-0. This wasn’t a sign of things to come for the Baggies, however, and they soon enjoyed their best start to a Premier League season as he was named Manager of the Month in September.
Managing Chelsea
In spite of how well Di Matteo had done at West Brom, a poor run of form in December and January resulted in him being relieved of his duties and replaced by Michael Appleton. The Baggies eventually finished 11th, with Di Matteo having laid the groundwork for it to such an extent that his reputation wasn’t diminished by the run of poor results. When Chelsea appointed Portuguese manager André Villas-Boas as the club’s manager in the summer of 2011, he decided that he wanted someone with experience of the club to come on board as an assistant, with Di Matteo soon emerging as the obvious candidate.
Villas-Boas never really won over the Chelsea players, with John Terry later explaining that a lot of it stemmed from him asking the senior players to fly in economy in pre-season with the junior players travelling in first class. Villas-Boas was sacked as Chelsea manager on the 4th of March 2012, with Di Matteo taking over as the caretaker manager. He won his first three games, which included defeating Birmingham City in the FA Cup, Stoke City in the Premier League and Napoli in the Champions League. The latter included a 4-1 win in the second-leg of the last 16 tie, with Villas-Boas’ team having lost 3-1 in the first-leg.
A 5-1 win against London rivals Tottenham Hotspur in the FA Cup semi-final helped him further his bond with players and supporters, whilst a win over Benfica in the Champions League set up a semi-final against holders Barcelona. The Blues won 1-0 in the first leg but looked doomed in the second when John Terry was sent off in the first-half at the Non Camp. Chelsea dug deep, however, and got a 2-2 draw to see them into the final. It was to be played against Bayern Munich in their home ground of the Allianz Arena, with the small matter of an FA Cup tie against Liverpool to be played first on the fifth of May.
Chelsea defeated Liverpool 2-1 in the final, setting them up nicely for their Champions League final match. It looked as though Bayern had won it when Thomas Müller scored for them in the 83rd minute, only for Didier Drogba to equalise five minute later and take the game to extra-time. Juan Mata missed Chelsea’s first penalty, but neither Ivica Olić nor Bastian Schweinsteiger could convert those whilst Chelsea’s remaining players did, seeing the club become the first London side to win the Champions League and allow Di Matteo to win the double during his first three months as the manager.
Life After Chelsea
Unsurprisingly given the success that he enjoyed, Di Matteo was made the permanent Chelsea manager in the June of 2012. The club lost the Community Shield to Manchester City, but defeated Wigan Athletic, Reading and Newcastle United in the Premier League. A 4-1 loss to Atlético Madrid in September was a blot in an otherwise good start to the season that saw four consecutive wins after that. A decline in form meant that Di Matteo was sacked on the 21st of November 2012, however, having lasted just eight months in the role. In what became one of the oddest parts of his time in charge, he continued to be paid £130,000 a week because no compensation package had been agreed.
That payment remained until either the June of 2014 or he got a new job, so it is perhaps no surprise that he didn’t take on a new managerial role until the October of 2014 when he became Schalke 04 manager. The team qualified for the Europa League and finished sixth, but Di Matteo resigned in the May of 2015. A year later, the Italian became the Aston Villa manager, but he was sacked in the October after a 2-0 loss to Preston North End. He remained out of work for several years but in the January of 2023 took on the role of Technical Advisor at South Korean club Jeonbuk Hyundai Motors.