Assistant head coach Cristian Stellini became the latest to issue an apology to Tottenham fans after Wednesday's 1-0 loss to Sheffield United saw hopes of lifting a domestic trophy go up in smoke again.
Harry Redknapp, Andre Villas-Boas, Tim Sherwood, Maurico Pochettino, Jose Mourinho, Nuno Espirito Santo and Antonio Conte have all overseen cup exits since Spurs last trophy in 2008.
The North London side have come close on several occasions, losing finals to Chelsea, Manchester United and Manchester City, as well as suffering six semi-final exits.
Yet Spurs have spurned several golden opportunities since Juande Ramos lifted the Carabao Cup, with inexplicable collapses, team selections and performances allowing the trophy drought to continue.