Di Matteo, watched by almost as many Italian media as English, struck with four minutes left of a disintegrating contest. Emerson, the Brazilian who had done so much to overthrow Chelsea's first-half dominance, gave away a throw-in. It was quickly given to Mark Hughes who curled a pass inside to Di Matteo 25 yards out. He shrugged off a challenge from Nick Barmby before driving the ball low inside Alan Miller's right-hand post.
Victory was just about deserved. Chelsea created enough chances, but looked like drawing their second successive blank. As at The Dell on Sunday, they started brightly but lost their rhythm in the face of increasingly competitive opponents.
Although Vialli does not yet appear fully fit, it increasingly appears that Chelsea have signed another Mark Hughes - a scorer of great goals rather than a great goalscorer. He again went spectacularly close, acrobatically volleying into the side-netting after 42 minutes, and will get his share of goals. But if Chelsea are to prosper, they will need a good number from midfield as well.
Ruud Gullit's return will help. He is still missed in midfield. He can argue - and did - that his presence as manager was seen in that last 10 minutes. Gullit has placed great emphasis on raising his players' fitness levels, and has employed Ade Mafe, the former Olympic sprinter, to that end.
When these teams met last February, Chelsea won 5-0 with Gavin Peacock scoring a hat-trick. Now he is on the bench and talking of a transfer. He is a victim of Chelsea's Continental drift, but it did not take long last night to thrill to the more positive consequences. Within three minutes, Juninho had tussled with Di Matteo and Ravanelli tackled Vialli. Who could have imagined such players at Stamford Bridge two years ago? It is only three months since the latter pair won the European Cup with Juventus.
Vialli was more prominent last night, but Ravanelli had the best chance, dragging his shot wide after breaking free on 34 minutes. Hughes missed Chelsea's best chance, shooting weakly over with 10 minutes left. Di Matteo had earlier brought a fine save from Miller.
There was one encouraging feature among the imports - Jody Morris, a 17-year-old former youth international, made a promising full debut. "Less than an hour before kick-off he had been getting autographs for his mates," Gullit said. "It shows talent has a chance at Chelsea. I don't just buy stars."
Chelsea (3-5-2): Kharin; Johnsen, Leboeuf, Clarke; Petrescu, Morris, Di Matteo, Wise, Minto; Hughes, Vialli. Substitutes not used: Duberry, Lee, Peacock, Nicholls, Hitchcock (gk).
Middlesbrough (3-5-2): Miller; Pearson, Vickers, Whyte; Cox, Mustoe, Emerson, Juninho, Fleming; Barmby, Ravanelli. Substitutes not used: Moore,Whelan, Hendrie, Branco, Walsh (gk).
Referee: G Willard (Worthing).Reuse content