Simon Milton has announced he is set to leave Town after 30 years, first as a player and then as part of the backroom staff, most recently working as the club’s director of academy sales.
The 53-year-old, who joined the Blues from Bury Town in 1987 for a fee of £5,000, revealed his exit in the latest academy newsletter: "I have decided that the time is right for me to leave my position as director of academy sales.
"This is not a decision I have taken lightly but one which I feel is right for me at this time.
"I will be very sad to leave the club after 30 years but will still attend home matches supporting the team and meeting up with you all in the new season.
"I am waiting for confirmation on how my existing role will be filled and I will let you know as soon as it has been agreed.”
Thanks to Managers, Teammates, Staff, Directors, Sponsors, Fans & Media for a brilliant 30yrs. #itfc #memories pic.twitter.com/8rkZVTUmkB– Simon Milton (@Milts25) June 8, 2017
Town MD Ian Milne said in a statement: "Simon Milton has decided to leave the club at the end of this month to take up a new challenge.
"He has been a fantastic and loyal servant to the club, firstly as a player for 11 years and then for another 19 years working on the commercial side.
"There is no doubt he will be missed and everyone at the club wishes him every success for the future.
"We do hope to see him back at Portman Road next season though, supporting Mick and the players.”
Milton made 258 starts and 72 sub appearances, scoring 56 goals, before retiring in 1998 following his testimonial season. He was a member of the 1991/92 Second Division championship-winning side.
While a Blues player the Fulham-born midfielder spent time on loan at Exeter and Torquay.
Milton, who also played locally in non-league for Thetford, the town in which he grew up, prior to his time with Bury, was inducted into the Town Hall of Fame in March 2016.
In February, he was made the guest of honour at the EFL Cup final by charity Prostate Cancer UK in recognition of the £250,000 he had helped to raise via their annual Amsterdam Cycle Challenge the previous three summers.