Italian midfielder, best known for his wonder goal for Chelsea against Middlesbrough in the 1997 FA Cup Final. Born to Italian parents in Schaffhausen, Switzerland, in 1970, Di Matteo started his footballing career for his local team before joining FC Zurich and Aarau, winning the Swiss League and Swiss Player of the Year award in 1993.
Following his successes in Switzerland, Di Matteo signed for Italian giants Lazio, and made his debut for the Italian national side soon after. Sadly (for Lazio), Di Matteo had personal differences with his coach, the former Czech basketball coach, Zdenek Zeman, and after being singled out for criticism after an embarrassing defeat against Internazionale, the now firmly established Italian international let it be known that he wanted a move away from the club. Chelsea manager Ruud Gullit stepped in, and before long Di Matteo was winging his way to West London, to the disgust of the Lazio faithful.
Di Matteo joined a host of new stars at Stamford Bridge, including Gianfranco Zola, Gianluca Vialli, Mark Hughes, Dan Petrescu, and of course the player-manager Ruud Gullit, still one of the finest players ever to kick a ball. Di Matteo's cultured passing and tenacious attitude added much needed bite to Chelsea's midfield, and although the club's league form was as unpredictable as ever, they soon became a formidable cup team.
This became apparent during the 1997 FA Cup campaign. Having spectacularly clawed back a 2-0 deficit to beat Liverpool 4-2 in the early rounds, Chelsea stormed through the remaining ties to reach their first Cup Final in 27 years with ease. Their opponents were Middlesbrough, who had signed a few international superstars themselves (Fabrizio Ravenelli and Juninho chief among them), but had had a terrible season, culminating in relegation from the Premiership. Their only hope of salvaging something from the season lay at Wembley, but their Cup Final optimism lasted for all of 43 seconds of the match.
That was how long it took Roberto to hammer home one of the most memorable goals in FA Cup history. Middlesbrough launched an attack, but immediately lost possession, and the ball found it's way to Di Matteo, 30 yards out, who lashed a piledriver over despairing goalkeeper Ben Roberts and in off the underside of the crossbar. The Chelsea fans, who had spent 27 years waiting for a stab at FA Cup glory, and then less than a minute to see it realised, fell into delirium, while the Middlesbrough team fell into catatonia, and the game was effectively over. Eddie Newton tapped home a second for Chelsea late in the game, but he needn't have bothered. Di Matteo had won the game long before, with the fastest goal in Cup final history.
Di Matteo went on to win the European Cup Winners' Cup and the League Cup with Chelsea the following year, and returned to Wembley for another FA Cup Final in 2000, this time against Aston Villa. Predictably, Di Matteo scored the only goal in that game (a slightly less spectacular effort following a typically calamitous goalkeeping blunder from David James).
Di Matteo's persistent injury troubles finally got the better of him the following season, and the talented Italian was forced to retire from the game at a comparatively early age. He now runs a pair of restaurants, one in Chelsea, the other in Mayfair. He is also, obviously, a Chelsea legend.