Founded in 1876, Boro had come close to a trophy a few years earlier, reaching both the FA Cup and League Cup finals in 1997, then returning to the League Cup final in 1998. In their first League Cup final, they led Leicester City 1-0 deep into extra time, but conceded a goal in the 118th minute to force a replay which Leicester won, 1-0.
Bolton, meanwhile, had won a slew of FA Cups (1923, 1926, 1929, 1958), but had reached the League Cup final only once before, losing 2-1 to Liverpool in 1995.
The teams met at Cardiff's Millenium Stadium, where many of the official 72,634 attendees missed the opening goal. In just the second minute, while they were still making their way to their seats, Boro midfielder Boudewijn Zenden fired a ball across the goal. It was met by his teammate, forward Joseph-Désiré Job (pictured, left), who turned it into the net to put Boro up 1-0.
Five minutes later, Zenden doubled the lead with a penalty kick after Bolton center back Emerson Thome fouled Job in the box. Even though Bolton pulled one back with a strike from Kevin Davies in the 21st minute, they could not get an equalizer past Middlesbrough keeper Marl Schwarzer and the match ended as a 1-2 Boro victory.
At the time, Job's goal was the quickest in League Cup history, but that record was later beaten by John Arne Riise, who netted for Liverpool in the first minute the next year.