The former Tottenham head coach led Aston Villa to a momentous victory over Liverpool in the FA Cup semi-final on Sunday.
His side now stand in the way of Spurs' bitter north London rivals Arsenal recording back-to-back FA Cup final victories.
Choosing between the two is surely no contest. Sherwood may be a source of slight irritation among Spurs fans for his recent insistence Harry Kane's success this season is down to him, but there is unlikely to be a Tottenham supporter who would rather Arsenal win the cup than he does.
Cheering on Sherwood to put a smile on Tottenham faces is not meaningless either. SkySports report that Tottenham need an Arsenal victory to qualify for Europe next season if Mauricio Pochettino's side drop a spot from their current position and finish seventh. With a match upcoming against competitors Southampton, it's a real possibility if they lose.
An Aston Villa win would remove that qualifying spot, who would not reach the Europa League if they lose to Arsenal, and the place would be awarded to the league's seventh placed team.
Is Europa League qualification really a prize? Tottenham's Premier League campaigns have been derailed in recent years by battling on multiple fronts, and a season without European involvement can only be of long-term benefit as they strive to qualify for a Champions League place in 2015/16.
Arsenal fans took great delight when Sherwood was Spurs boss at claiming the current Villa man as being a fan of the Gunners, drawing attention via social media a previous interview broadcast where he discussed his affection for the club.
But on Saturday May 30th, Sherwood is likely to be reclaimed as one of Tottenham's own, to prevent Arsenal success and just perhaps ensure a Europa League-free season.