At 20 in the countdown is a defender who remained a stalwart of the side for over a decade, making over 500 appearances in the process.
Gary Kelly lived the full roller coaster of emotions that Leeds United went through during the 1990s and early 2000s, having been a youngster making his first appearances for the club during their title-winning campaign of 1992, helping the Whites almost conquer Europe and then watching it all come crashing down.
The defender moved to Elland Road in 1991 having initially begun his career in Ireland as a striker. However, he was quickly moved into the back line and went on to appear twice as Leeds won the final First Division title before the dawning of the Premier League era.
Despite not appearing throughout the next campaign, he established himself as first-choice in the 1993-94 season. And his solid performances were recognised as he was included in the PFA Team of the Year.
He would remain an almost-permanent member of the side for the next four years, being made captain under George Graham for the 1997-98 campaign. While Lucas Radebe would soon take over skipper duties, Kelly was always ready to take back the armband when the South African had to disappear for a poorly-timed international fixture.
The Republic of Ireland international - who earned 51 international caps and would play at two World Cups - would remain a key member of the side that would reach the Champions League semi-final in 2001 and remain a constant threat in the league during that time.
Unlike many of his teammates, Kelly stuck around when the club's financial implosion led to relegation from the top flight, and was almost rewarded as United came within one game of returning to the big time in 2006. However, they were dismantled by Watford in the play-off final.
His final season before he retired aged just 32, saw him make just 16 league appearances as he fell out of favour with the club's hierarchy. Sadly, and arguably unbefitting of the service he had given to the team, Leeds ended the campaign having been relegation to the third tier.
Although Kelly's contribution often went unappreciated by many - with his nephew Ian Harte often stealing most of the headlines for his set-piece taking prowess - his consistent ability to keep some of the best wingers the Premier League had to offer quiet was a key part behind the team's success around the Millennium.
And having made over 500 appearances for the club, and not jumping ship when United went down, there is no doubt that cult-hero status is assured for the defender.