Wimbledon pulled off one of the biggest upsets in the tournament's history when they beat Liverpool 1-0 to lift the trophy in 1988.
The club subsequently fell into decline before a controversial relocation to Milton Keynes in 2003, with a rebrand to MK Dons following in 2004.
Fans opposed to the relocation formed their own club – AFC Wimbledon – in 2002, and have seen the new side force its way into the Football League during just 12 years in existence.
And Scales, who came off the bench for Wimbledon in the 1988 final before going on to join Liverpool six years later, believes Monday's clash at Kingsmeadow will stir fond memories for fans of AFC Wimbledon and its predecessor.
"It's a great moment for AFC Wimbledon," he told Perform. "It's obviously such an iconic game in everyone's memory from '88.
"The whole rebirth and formation through the fans of the new Wimbledon club and the journey they've been on for the last 10 years or so - to have this moment is very special for them.
"I know a lot of people there and I've got a great affinity with them because there are so many familiar faces who are still a part of the club.
"The whole story is a fantastic one."
Despite the gulf that currently exists between clubs in the English football pyramid, Scales - currently an ambassador for the Football Foundation, which has helped transform grassroots facilities in the sport since 2000 – believes it would be foolish to write off AFC Wimbledon.
"You'd expect Liverpool to go down and win, of course you would, but I know more than anybody what shocks and upsets you can get in the FA Cup," he added.
"Liverpool will be anxious about approaching that tie. Obviously playing at Kingsmeadow, the pressure is on Liverpool because it's a no-win situation.
"Conversely, it's a no-lose situation for AFC.
"When you add in all the dynamics of the classic FA Cup tie, it's got the ingredients of a great, great game.
"The fans are going to absolutely relish this match and it will bring back so many great memories of '88.
"It will be the culmination of this incredible journey that they've been on and the steps they took on Wimbledon Common so long ago when they formed the new club.
"I can't wait to be down there to take in that atmosphere within the whole context of revisiting '88, which I haven't done that much over the past 25 years or so."
Scales was also part of the Liverpool side that lost 1-0 to Manchester United in the 1996 FA Cup final.
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