Glyn Pardoe, a member of Manchester City's 1968 league-winning side, has died at the age of 73, the Premier League club have announced.
Pardoe spent his entire playing career with City between 1962 and 1976, and scored the winning goal in the 1970 League Cup final.
"Everyone at City is deeply saddened to learn of the passing of Glyn Pardoe," City wrote on Twitter.
"Our thoughts and condolences go out to his friends and family at this difficult time."
Pardoe remains the youngest player to turn out for City, having made his debut against Birmingham in April 1962 at the age of 15 years and 341 days old.
The left-back went on to make 380 appearances for the club during their successful period in the late 1960s, winning the league title in 1968, the FA Cup in 1969, and the League Cup and European Cup Winners' Cup in 1970.
But Pardoe broke his leg in a tackle with George Best during a Manchester derby in 1970 and struggled to regain his place in the side after a lengthy lay-off. He later took up a coaching position with the club after retiring from playing.
City was a family affair for Pardoe, whose cousin Alan Oakes was a team-mate throughout his playing days.
Pardoe's daughter Charlotte is married to Scott Doyle, the son of Pardoe's late team-mate Mike Doyle, and both men were grandfathers to Tommy Doyle, the 18-year-old midfielder who made his debut for City in a 3-1 League Cup win over Southampton in October last year.