Thursday night's fixture between England and Wales at Wembley will be the first meeting between the sides since the Three Lions thumped Rob Page's men 3-0 in Qatar to bring an end to the Dragons' bitterly underwhelming 2022 World Cup.
Marcus Rashford netted either side of Phil Foden's effort at Al Rayyan's Ahmad bin Ali Stadium to ensure Wales finished rock bottom of their group having scored just once and gained only one point from a possible nine in what was only their second ever appearance in the global showpiece, and a first since 1958.
But the true gut-wrenching moment came little more than two months later when talisman Gareth Bale - scorer in Wales' World Cup opener against the USA - announced his retirement from football.
That was soon followed by the international retirement of Joe Allen, who later resumed his Wales career but has since brought an end to his playing days entirely.
It truly represented a changing of the guard, and with Wales going on to miss out on qualification for Euro 2024 in Germany, Page lost his job.
Craig Bellamy, who recently passed a year in the role of Wales head coach, has focussed on building a whole team and a squad capable of challenging as opposed to relying heavily on individual talents.
But how do the current crop stack up to those who did the unthinkable by beating Austria and Ukraine in the play-offs to end their nation's 64-year wait to qualify for a World Cup just over three years ago?
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Only 14 players (Danny Ward, Adam Davies, Ben Cabango, Ben Davies, Chris Mepham, Joe Rodon, Neco Williams, Ethan Ampadu, Sorba Thomas, Harry Wilson, Rubin Colwill, Mark Harris, Brennan Johnson and Kieffer Moore) in Bellamy's squad to face England and then Belgium in a World Cup qualifier this month were part of the 26-man group Page took to Qatar in 2022.
There has been a real emphasis of late by Bellamy to give young talent the opportunity to impress, as evidenced by Cardiff City's 19-year-old centre-back Dylan Lawlor who produced a man-of-the-match display on debut against Kazakhstan in September.
His Bluebirds team-mates Ronan Kpakio, Isaak Davies and Joel Colwill have also come into the fold of late, while Swansea City's Liam Cullen, Stoke City's Sorba Thomas and Bolton Wanderers midfielder Josh Sheehan - who had all previously won caps - have had more opportunities to showcase their talents under Bellamy.
Page received plenty of flak for his use of the word transition in the latter stages of his tenure as manager of his country, but as Bellamy's ever-evolving squad has shown, change certainly was needed to make Wales as competitive as possible in the post-Bale era.
The 46-year-old has overseen an encouraging run of six wins, four draws and just one defeat from his 11 competitive matches as boss so far, although his side's most recent outing was a 1-0 friendly loss to Canada in Swansea.
It means Wales remain firmly in contention to secure a top two place in their World Cup qualifying group, with Monday's contest with Belgium at Cardiff City Stadium likely to prove decisive in determining whether or not Bellamy's side will stand a chance of topping Group J next month.
The upcoming double header is by some distance the toughest of the Bellamy reign so far and will truly show whether or not Wales can compete with the best in the game.
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Indeed, Bellamy has fluctuated between proudly revealing he chose Thomas Tuchel's side as their opposition before conceding that a boxing promoter would not set up a clash between the teams - such is the gulf in quality between the pair.
So a first victory over the 'old enemy' since 1984 seems unlikely, to say the least - even more so when you consider that Belgium's visit to the Welsh capital four days later has significantly more riding on it.
But the current international camp will say a lot about the progress and where Wales truly are more than three years on from the retirement of their greatest ever player.
