First team players Ryan Bertrand and Oriol Romeu are among seven senior players that have their contract expire in the summer of 2021.
Southampton, who also have club record transfers Sofiane Boufal and Guido Carrillo going into the last 10 months of their current deal, will look to resolve the contract issues as quickly as possible to avoid letting players leave on a free next year.
Full-back Bertrand has been a key part of the Southampton squad since his arrival in 2014, with the defender making at least 30 league appearances in five of his six seasons at the club.
In his time at the club, the former Aston Villa man has been an integral part of back-to-back record points tallies in the Premier League, as well as two Europa League campaigns and a Carabao Cup final.
Originally joining on loan from Chelsea before making the permanent switch in 2015, the defender has been entrusted at left-back under five different managers, forcing former understudy Matt Targett to leave the club in search of first-team football last summer.
The former Saints' captain has been a reliable figure this season, with his defensive output a particular strong point. His 2.7 tackles and interceptions per game rank slightly higher than that of Andrew Robertson and Ben Chilwell, with his post-lockdown performances playing an integral role in Southampton's success.
According to The Athletic, the Saints have already offered Bertrand a new contract, with the club expecting him to sign the deal.
It is understood that the contract that has been offered is a three-year contract extension.
Fellow Champions League winner Romeu has endured a similar path to that of Bertrand whilst residing on the south coast.
The Spaniard, who joined a year after his former Chelsea teammate, has been an important member of the squad since his arrival, even though he has not always been the first choice.
Despite having spells out of the team under Mark Hughes and current manager Ralph Hasenhuttl, the midfielder has still been able to accumulate 189 league appearances with the club over five seasons, with his debut campaign under Ronald Koeman the only time he has not played in at least 30 league games in a single season.
With Pierre-Emile Hojbjerg departing the club for Tottenham, and with Romeu starting each of the last five matches of the 2019/20 Premier League season, it could be considered that the 28-year-old will be given a chance to prove himself in Ralph Hasenhuttls 4-2-2-2 system next season.
However, with the Saints being linked with midfielders such as Weston Mckennie and Oliver Ntcham, it seems that the Austrian manager is looking for a younger, more versatile and athletic midfielder that will contribute both in a defensive way, but also has the technical ability to progress the ball up the pitch and help with the attacking play.
Coming on as a substitute after the 75th minute on eight occasions during the season (with Southampton winning on six of those), Hasenhuttl uses the former Barcelona man as a ball-winning midfielder late on in tight matches to help support the defense and break up opposition attacks, with little to no attacking responsibility with the Saints not looking to risk the lead that they already have.
According to the Telegraph's Jeremy Wilson, the Saints are looking to renew Romeu's contract.
A man unlikely to sign a new deal with the club is Harrison Reed. Despite The Athletic reports that the 25-year-old was going to be given a chance in pre-season after a successful promotion campaign out on loan with Fulham, the absence of a squad number for the midfielder would say otherwise.
Such a switch comes without surprise, with Reed far from guaranteed first-team football at Southampton. Even with the departure of Hojbjerg, the emergence of 20-year-old Will Smallbone, the return to the first team of Romeu, and the Saints' desire to sign a new central-midfielder, Reed would once occupy the bench more than the football pitch.
However, it could be considered that the quick nature in which Reed was overlooked by Hasenhutl was harsh, with his style of play fitting to the Southampton system.
His 3.3 tackles and interceptions per game is similar to that of Hojbjerg, with his terrier-like midfield approach fitting to that of Southampton, with players expected to win the ball back as fast as possible when possession has been lost.
Argentine Guido Carrillo is another man that will not be at the club after June 30th, 2021.
Signed for a record £19m fee in 2018, the former Monaco striker was brought in my Mauricio Pellegrino to bolster the attacking options and save the Saints fortunes, with Southampton winning just four of 25 games up until his signature.
Eight games after his debut for the club, Pellegrino was sacked and replaced by Hughes. Carillo played just two games under Hughes, with his appearance against West Ham in 2018 the last he would make for the club.
The following two seasons would see the 29-year-old go out on loan to Leganes, scoring seven goals in 56 games.
With no interest in keeping the striker, so much so that Southampton have not given him a squad number for the upcoming season, the desire to cut losses and get his reported £65,000 wage off of the books.
A former club-record signing Boufal is also entering the final year of his five-year contract, with no news of a new contract on the table so far.
Signing for a reported £16m fee in 2016 from Ligue 1 side Lille, the Moroccan has quite an indifferent time on the south coast.
Playing 70 league games for the club, an output of three goals and four assists does not seem deserving of a new long-term deal, but the idea of the winger departing the club, especially on a free in the summer, would be less than impressive.
His skillful dribbling ability and creative knowhow to create something out of nothing brings something that no other player in the squad has, but the sporadic nature in which this appears has certainly underwhelmed the Southampton faithful.
In extension, the Saints’ do not seem to be able to give the 26-year-old the regular first-team football that he desires. The impressive form of Nathan Redmond and Stuart Armstrong at the end of the season will almost certainly mean that they start the season as the preferred attacking midfielders, the versatility of youngster Smallbone, and the strong debut season for Moussa Djenepo despite limited minutes means that the former Celta Vigo player could start the season as the fifth choice attacking midfielder.
The Southampton trifecta of Sam McQueen, Josh Sims, and Jake Hesketh are all set to leave the club, with all three failing to be given a squad number before the start of the 2020/21 season.
After an impressive 2016-17 under Claude Puel, where McQueen was handed 20 appearances in all competitions, transitioning from a winger to a left-back, the arrival of Pellegrino effectively ended all ambition of becoming a regular for the Saints’.
Handed just six league games under the Argentine, the former England youth international was sent out on loan the following year to gain first-team experience.
However, the loan ended abruptly, with the Englishman suffering an ACL injury in a Carabao Cup match on November 1st, 2018 whilst playing for Middlesbrough. McQueen has not played since.
With heavy competition in the attack, and Jake Vokins playing as a backup to Bertrand at left-back, it is unlikely that Southampton fans will see McQueen play for their side again.
Sims was a winger that impressed at times, especially when driving forward with the ball, but his inconsistent performances meant that he was never able to nail down a first-team place, with a less than impressive loan spell at Reading in the 2018/19 season not helping his case on return to Southampton.
However, there will most certainly be a home for Sims should be depart, with the New York Red Bulls a keen admirer of the player.
Hesketh will also leave, with the youngster making just three first-team appearances for the club (none in the league), with loan spells at Burton Albion, Milton Keynes Dons, and Lincoln City not enough to sway the Southampton hierarchy into giving him a chance.