The Hearts assistant manager has twice reached the final of this competition and, on both occasions, he has been on the losing side.
Brown was Kilmarnock assistant to his long-time colleague Jim Jefferies in 2007 as Hibernian dismantled the Ayrshire outfit 5-1 at the national stadium. "A really bad day," according to the veteran coach.
Eleven years previously, he was in the dugout as Hearts assistant as Paul Gascoigne turned in a mesmerising display at Celtic Park for Rangers to secure a 4-3 triumph in one of the greatest League Cup finals of all time.
It is an indictment of Brown's tortuous League Cup experience that he actually lists that defeat by the Ibrox side as his best memory in the competition.
"We were down 2-0 and got it back to 2-2. Paul Gascoigne clicked into action that day, but it is a game I remember for the performance of Neil McCann. Neil and the whole team were immense, that day. I suppose that would be my best memory, but even that was in defeat.
"I would certainly hope we could go on a good run this year, this is a real chance to get to the quarter-final."
There's no doubt another cup run would aid the administration-hit capital club, with a lucrative quarter-final tie waiting in the wings if they can dispose of Queen of the South this evening.
Much has been made of the inexperience of the Hearts players this term, but Brown insists this is proving to be a positive outcome. "We have a group of young lads and their enthusiasm and lack of fear is an advantage to us," he said. "Playing at Tynecastle at the moment is nothing but a pleasure."
Hearts' opponents tonight will arrive in the capital in optimistic mood, however, with Queen of the South buoyed by their 2-0 win over Morton at the weekend - their first victory since knocking Scottish League Cup holders St Mirren out of this season's competition in the last round.
Jim McIntyre, the Queens manager, said: "We have done well in cup ties this season and it was great to defeat St Mirren, but we are the home of a bigger boy this time. Hearts are playing with a great spirit just now and the pressure is on them to win. So we can simply look to go out and enjoy it. If they have an off night we are capable of getting a result, but it will be difficult. We are going there after a good result at Morton so we have nothing to fear."
Queens will take almost 1000 supporters to Tynecastle tonight but could be cheered on by more after Hearts agreed that a cash turnstile will now be in operation for travelling supporters.