The Saints' scouting network turned up gems like Sadio Mané, Virgil van Dijk, Victor Wanyama, Graziano Pelle and Dejan Lovren, while their academy churned out stars in James Ward-Prowse, Adam Lallana, Luke Shaw and Calum Chambers.
Inevitably, Southampton's crown jewels were picked off one by one – mostly by Liverpool – and they could not maintain their success in the transfer market.
Mauricio Pochettino and Ronald Koeman were also shrewd appointments, but Mauricio Pellegrino and Mark Hughes backfired spectacularly and things spiralled.
That was until the arrival of the ‘Alpine Klopp'. Ralph Hasenhüttl revitalised the ailing Saints and staved off the threat of relegation after being appointed on December 5. The club heads into the new season with renewed optimism.
Now with a new chairman, Jisheng Gao, vice-chairman, Nelly Gao, and chief executive, Martin Semmens, a clear-out is anticipated with at least five first-team players set for the axe, according to the Daily Telegraph.
With that in mind, we've gone through Southampton's squad with a fine-tooth comb to identify the players most at risk…
A member of England's 2014 World Cup and 2016 European Championship squads, the giant Geordie made his only appearance in 2018/19 on the final day of the season and looked shaky at best.
Displaced by Alex McCarthy after a 5-2 thrashing at Tottenham Hotspur in December 2017, Forster did not make another first-team appearance until the 3-0 defeat by West Ham United on the final day of last season.
Angus Gunn ended the campaign as the Saints' No.1 and with three senior goalkeepers on the books, something has to give this summer. Forster, having endured a dramatic fall from grace, looks most likely to give way.
The forward might have provided one of the viral moments of the 2018/19 campaign with his post-match rant following a disallowed goal against Watford, but it was another forgettable season in front of goal for the 29-year-old.
With just two strikes to his name from 25 appearances and just 16 in 71 outings during three-and-a-half injury-plagued years at St Mary's, Austin has struggled the transfer the form he showed at Queens Park Rangers and Burnley.
A new striker is thought to be near the top of Hasenhüttl's wanted list and Austin is a prime candidate to make way.
But the full-back ended the season on loan at Internazionale with young Frenchman Yan Valery taking his place in the team. Having impressed Hasenhüttl sufficiently over the next six months, making 24 appearances in all competitions, Valery's progress would be hampered if Cédric returned to St Mary's this summer.
Although he featured sparingly while on loan at Inter, making just four Serie A appearances, the 27-year-old is in the peak of his career and should fetch a handy fee for the Saints if the right buyer can be found.
Non-Southampton supporters will be forgiven for responding ‘Who?' at this juncture. The Norwegian winger-cum-forward joined from FC Basel for £16million last summer and is one of the ‘legacies' of Hughes' ill-fated reign.
His record in Switzerland was impressive for a wide player, netting 21 times in 56 starts. But it did not extend to the Premier League. In 16 appearances, of which only eight were starts, Elyounoussi failed to score and registered just 20 shots – only six of which hit the target.
Unsurprisingly he was quickly ousted from the side and made his final league start on December 30 against Manchester City. Another one seems unlikely.
Being signed to succeed Virgil van Dijk puts a lot of responsibility on a player's shoulders. A responsibility which Hoedt never really looked comfortable with and, beyond the fact they were both Dutch, the two had little in common.
Hoedt failed to deliver on that price-tag, though, and any likeness to countryman Van Dijk was forgotten almost immediately as he blundered his way through 45 appearances for the Saints before being loaned to Celta de Vigo in January.
Sent off on his debut, the Galicians won't be taking up their permanent option.
Continuing the theme of strikers who couldn't hit a barn door, Argentine Carrillo was supposed to be the missing piece of the jigsaw for Pellegrino having played under him for Estudiantes – a signing which appeared to indicate the club's board would keep faith in their under-fire manager.
The 28-year-old was never prolific in his homeland, netting 37 times in 132 outings at a rate of one every three-and-a-half appearances, before bagging just 21 in 95 for Monaco. Somehow les Monegasques persuaded the Saints to part with £19million in January 2018 – presumably laughing all the way to the bank.
Carrillo failed to pull up any trees in England and after eight goalless appearances, Pellegrino was sacked. He appeared just twice more for the Saints before following his No.1 advocate to Leganés where he managed six in 31 LaLiga outings last term.
Whatever happens next for the Paris-born Morocco international, he will always have that goal against West Bromwich Albion to hang his hat on.
Slaloming through the Albion defence from a starting point inside own half, in the space of a few seconds, Boufal lit up one of the worst Premier League clashes of all time and showed why the Saints forked out a then club-record £16million to sign him from Lille.
At the same time, that fleeting moment of genius underlined exactly why Boufal failed to deliver on his enormous promise while on the South Coast. It was his one and only memorable contribution in a Saints jersey.
Like Cédric, Hoedt and Carrillo his escape strategy has already begun with a loan switch to Celta where he bagged two in 19 last term.