Liverpool have confirmed that James Milner, Roberto Firmino, Naby Keita and Alex Oxlade-Chamberlain will depart the club when their contracts expire at the end of the season.
The quartet, all of whom have been at the club when the Champions League, Premier League, FA Cup and League Cup have been won by the Reds, leave on free transfers ahead of a busy transfer summer on Merseyside. Between them, they have made 965 appearances for Liverpool.
Milner and Firmino were the longest-serving of the pair, with both joining the Reds in the summer of 2015 when Brendan Rodgers was still in charge.
Former Leeds, Aston Villa, Newcastle and Manchester City midfielder Milner, 37, served as Liverpool's vice-captain under Jurgen Klopp and has played 330 times for the Reds in a variety of positions.
The veteran was seen as the epitome of professionalism during his time on Merseyside and is credited with helping to set the standards which drove the Reds towards winning the Champions League in 2019 and the Premier League a year later.
Firmino, who joined from Hoffenheim in 2015, found his feet following the appointment of Klopp as Rodgers' successor and quickly became a key player for the Reds boss as he used him in a false No.9 role to implement his pressing game.
The forward, who is the highest-scoring Brazilian in Premier League history, scored 109 goals in 360 Reds appearances and formed a formidable front three with Sadio Mane and Mohamed Salah when the pair joined the club in 2016 and 2017 respectively.
As well as contributing key goals en route to Champions League and Premier League success, Firmino scored in the semi-final and final of the Club World Cup as the Reds won the trophy for the first time in December 2019.
Keita signed for Liverpool on a pre-contract agreement in the summer of 2017, eventually joining the club from RB Leipzig a year later for a fee of £52.75m.
The Guinean midfielder arrived with a big reputation and was seen by many as the replacement for Philippe Coutinho, who joined Barcelona in a £142m deal in January 2018.
The 28-year-old did have his impressive moments in a Liverpool shirt, but was frequently troubled by injuries and is currently sidelined having scored 11 goals in 129 appearances for the Reds across his five seasons at the club.
Oxlade-Chamberlain joined Liverpool from Arsenal in the summer of 2017 and initially impressed as he took up a key role in Klopp's side in the 2017-18 season as they reached the Champions League final.
However, a serious knee injury in the semi-final win over Roma ruined his progress and saw him miss almost the entirety of the following campaign.
He did return to feature 30 times in the Premier League when the Reds won the division in 2019-20 but has largely been on the fringes of the side due to injury and lack of selection ever since. Oxlade-Chamberlain has played 146 times for Liverpool, scoring 18 goals.
The departures of all four players, particularly the midfielders, is set to herald a key summer of transfer activity for Klopp and Liverpool as they bid to return to the summit of the game at home and in Europe.