The Blues would go on to lift the trophy that season after beating Arsenal at Wembley, but came within a matter of seconds of being knocked out by the Bees at St Andrews that night.
Andy Scott's men had already been on a giant-killing run, knocking out Premier League side Everton and Championship outfit Hull City, who had just been relegated from the top flight.
They fancied their chances of another scalp at St Andrews, and silenced the home crowd when Sam Wood gave them the lead on 68 minutes.
League One Brentford were more than holding their own, and it was extremely harsh on them when Kevin Phillips struck an injury time equaliser.
Extra time failed to separate the sides, and so the game went to penalties, where Birmingham triumphed 4-3 after Michael Spillane and Craig Woodman missed their spot kicks.
Scott was hailed as a hero that night, but a fortnight later, a bizarre outburst after Brentford were on the receiving end of another giant-killing, being dumped out of the FA Cup by League Two Aldershot, spelt the beginning of the end for him.
His four-year tenure as Bees boss was over less than three months later following a dismal 4-1 defeat at Dagenham & Redbridge which threatened to suck them into a relegation battle.
In came Nicky Forster, assisted by current manager Mark Warburton, as caretaker to guide Brentford to safety as well as the JPT final, where they lost to Carlisle at Wembley.
The Carling Cup meeting was the first time the Bees had met the Blues since April 1995, when goals from Kevin Francis and Liam Daish saw Birmingham win 2-0 at St Andrews, and ultimately pip Brentford to the old League Two (third tier) title.
With only one team going up that season due to the Premier League being restructured, the Bees missed out on automatic promotion and crashed out of the play-offs to Huddersfield. It would be another 20 years before that wrong was put right.
Overall, the two teams have met 30 times, with Birmingham winning 15, Brentford nine and six finishing with honours even. You have to go back to December 1992 for Brentford's last win, a 3-1 victory at St Andrews in the old Division One (second tier).