If recovering from a two-nil deficit against a club that usually plies its trade in the Champions League wasn't challenging enough, Harry Redknapp will attempt to mastermind a remarkable recovery this evening without the majority of his senior players.
Much has been made by the lack of respect shown towards a competition which Harry has made his lowest priority, but at least this week the excuses stand up to scrutiny. In three days time we take on Manchester United at Wembley.
With a full strength side the task would prove difficult. Without the likes of Luka Modric, Robbie Keane, Roman Pavlyuchenko, Ledley King and Jonathan Woodgate it looks nigh on impossible, but at least the seemingly the insurmountable odds might inspire a refreshing all-guns-blazing approaching from the motley crew who do manage to take the field.
For these band of brothers, the match represents the last audition for a place at Wembley. Expect to see a blood and thunder display from Jamie O'Hara, who returns from a hip problem picked up in the semi-final "victory" at
The list of those unavailable is so extensive it would take less time to list the players who can play.
Gomes will definitely start, after injury ruled Carlo Cudicini out of both games. He is likely to be the one flailing at crosses just behind a rapidly stitched together back four containing Pascal Chimbonda, Michael Dawson, Gareth Bale and Chris Gunter.
Big name absentees could even lead Redknapp to take the unprecedented step of naming two 17-year-olds - John Bostock and Dean Parrett - in central midfield.
The importance of youth is not lost on Redknapp. Neither is the club's poor recent history of producing quality young players through the academy system.
"It is something that we need to do," Redknapp explained before this evening's game. "We need to start producing some players at this club again."
"We know the Hoddles the Perrymans, all of those lads…John Pratt, way back, you've had them over the years.
"There are too many to mention who have come through the conveyor belt of Tottenham - the club used to produce their own players for years. That has dropped off and we need to get it going again."
When Juande Ramos was in charge rumour had it that he did not rate a single member of the clubs youth squads. However, the likes of Dean Parrett, John Bostock and Danny Rose have given Redknapp cause for optimism.
Yet all of these players were purchased from clubs in the lower reaches of English football, rather than the club's own youth structure.
Their origin aside, Bostock and Parrett will likely be joined in the squad by a handful of other players from the club's in-form youth team. The side, coached by Alex Inglethorpe, sits top of its regional league and will play Arsenal in the FA Youth Cup quarter-final next Thursday.
"It's a chance to see some these kids play," explained Redknapp. "We'll get some answers because if they are going to be top players, then they will be good enough at 17, 18.
"It will be a great experience for them to run out at
"I could have played Gilberto [in
It's the sort of attitude that will get fan's pulses racing, and who knows, a good performance tonight could set up a dream appearance at Wembley for one of Redknapp's rising stars.