The quartet played 661 times for us between them and include two players who came through the Academy ranks in Jake Livermore and Ryan Mason, Tom Huddlestone, who spent eight years with us and fans' favourite Michael Dawson, who proudly captained the team in 324 appearances between 2005-2014.
It can be quite a strange experience for players, suddenly locking horns with players who they once went into battle with, so to speak.
Below: Ledley up against Peter Crouch, Spurs v Stoke
It's a scenario our legendary former skipper Ledley King knows well as he came up against the likes of Bobby Zamora and Jermain Defoe - strikers who played for the same Senrab youth team - and Peter Crouch, who played for Popmey and Liverpool before rejoining his close friend and fellow Academy graduate Ledley at Spurs in 2009.
"It is strange," said Ledley. "The first few times it’s difficult but after that, it becomes easier.
"Crouchy is such a nice guy, we came through the youth system at Spurs together and it was always difficult playing against him.
"Then there's Bobby Zamora, I knew Bobby as a young lad growing up and when you’ve got someone asking ‘how’s your mum?’ on the pitch, it’s not really what you want to hear when you are in battle mode!
Below: Ledley takes on Bobby Zamora - Spurs v Fulham
"I found it quite difficult. In fact, I would prefer not to know the opposition strikers at all, but you do get used to it with more experience.
"I’m sure the lads will enjoy this game against Hull, especially the likes of Harry Kane and Michael Dawson, who will face each other at close quarters, but at the same time, I bet they both wish they were playing against someone they didn’t know so well!"
Look out for Ledley's analysis of Harry Kane up against Michael Dawson tomorrow...