The 23-year-old Southampton star, who is the son of former Wimbledon forward Alan, joined the west Londoners aged nine and went on to graduate from their academy system.
However, Cork never made a first-team appearance for a Blues side awash with star names following the arrival of billionaire Roman Abramovich.
He went on loan to six different clubs in a bid to impress before eventually making a permanent move to Southampton in 2011. Cork gets the opportunity to face Chelsea for the first time tomorrow in an FA Cup third round tie at St Mary's and admits it is a special game for him.
"I am looking forward to playing against them," he said.
"I never got the opportunity to play with them when I was there so hopefully we can go and put a good performance in. I am looking forward to seeing some old faces.
"The main person I still speak to there is Ryan Bertrand. He was sort of the same age as me and has had some good performances and been able to get a few little runs in the team.
"It will be good to see him and a few of the older players as well as they were quite good to me when I was at Chelsea."
Cork highlighted Frank Lampard, John Terry, Ashley Cole and former Chelsea striker Didier Drogba as those that had the biggest influence on him.
"Jose Mourinho was manager when I was there and (current Liverpool boss) Brendan Rodgers was doing some of the coaching," he said.
"To have them coaching there as well as the likes of John Terry, Frank Lampard and Ashley Cole to get advice off every now and again was great.
"They have players that you can look up to that are so good, won so much and are such great professionals. It was great having them around.
"I was only really involved in the pre-seasons, with one trip to Los Angeles and a couple of friendlies here and there.
"The main thing that stuck in my head was Didier Drogba pulling me aside and giving me advice on how to defend against him and other bigger players.
"Just having advice like that from people who have done so much in the game was great and invaluable."
Cork will likely get an opportunity to show his former club what they are missing on Saturday.
Saints manager Nigel Adkins pledged to name a strong side against the FA Cup holders, who are reeling from a shock 1-0 home defeat to rivals QPR.
"I think they'll be out to prove a point," Cork said.
"Some people are convinced they played a weakened side against QPR, but whichever side they put out it's never going to be a weak team so hopefully we could take advantage if they're on the start of a bad run.
"We could look at it either way, but there's not much pressure on us really.
"A cup run would be great and it could help our league form, but the league is our main priority at the minute, and that will be our main focus."
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