Sherwood became boss at Villa Park on Valentine's Day but there has been little to warm the hearts of the fans since.
Villa have only won three of their 10 home Premier League games since Sherwood arrived and have made their worst start to a league season since 1986-87 so Tuesday's meeting with their old enemy from across town in the League Cup could be a turning point in their relationship.
The last thing Sherwood needs is another home derby defeat after losing 1-0 to West Bromwich Albion on Saturday.
That result left Villa with four points from their opening six games and without a win since they beat Bournemouth on the opening day of the season, leaving only Stoke City, Newcastle United and Sunderland below them.
"It was a very disappointing result against a local rival but I don't actually think we have achieved the points tally we deserve," Sherwood told reporters on Monday.
Villa were booed off on Saturday, but asked if his honeymoon period was over, he said: "No, I know what this game is like and a week is long time in football."
Birmingham and Villa have not met since the 2010-11 season, before Birmingham were relegated from the Premier League, but their derby is one of the fiercest in England, dating back to 1887 when Villa won the first of their 120 meetings, beating the Blues 4-0 in an FA Cup match.
Birmingham beat Villa 2-1 in their last League Cup meeting in December 2010 before going on to beat Arsenal in the final, their first major trophy since they beat Villa 3-1 on aggregate in 1963 when the final was played over two legs.
Blues boss Gary Rowett has sympathy for his opposite number but fancies his side's chances after making a solid start to the Championship campaign.
"We all understand that coming to Villa at the moment is not an easy job," he said. "Losing some of the players they lost in the summer like Christian Benteke and Fabian Delph makes the job doubly hard and while I wish him all the best, obviously, we are coming to do what we can do to get a result."
(Reporting by Mike Collett; editing by Martyn Herman)
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