Manchester City have confirmed the departures of winger Jesus Navas and left-back Gael Clichy.
Both players were out of contract this summer.
Navas spent four years the club, making 77 Premier League starts, with Clichy leaving after six years' service and more than 200 appearances.
Their exits follow that of long-serving right-back Pablo Zabaleta, who left after nine years at the club following the end of the season.
The futures of influential midfielder Yaya Toure, defender Bacary Sagna and goalkeeper Willy Caballero are also uncertain as they come to the end of their deals.
Navas, 31, was signed from Sevilla in 2013 and scored four goals for City. There were reports he could be offered a new deal at the Etihad Stadium but the Spanish World Cup-winner has also been linked with a return to his hometown club.
He helped City to the Premier League title in 2014 and enjoyed League Cup success in that same season as well as last year.
Manager Pep Guardiola experimented with him as right-back towards the end of the 2016-17 campaign but the club and player will now part ways.
City director of football Txiki Begiristain said: "Working with Jesus has been a pleasure.
"His hard work, dedication, professionalism and desire to win have been apparent every single day."
Clichy featured in two title successes and also won the League Cup twice after his move from Arsenal in 2011.
The Frenchman, 31, told the club's website, www.mancity.com: "It's been a special six years for me at City.
"To win four major trophies and help establish the club as one of the top teams in English football has been an incredible journey that I'm proud to have been a part of.
"It's amazing to see where the club is today and I am sure there is plenty more success to come."
Begiristain added: "Gael has been an important player for this football club and I want to wish him well for the future.
"Since my first day here, he has been an outstanding in the way he has applied himself, both in games and in training.
"He has been a key part in some special moments for this football club and for that he will always be remembered fondly."
The departures are expected be the start of an overhaul of the squad as Guardiola looks to rebuild following an underwhelming first campaign at the club.
There are a number of other players out on loan who could also move on, including Samir Nasri, Joe Hart, Eliaquim Mangala and Wilfried Bony.