Middlesbrough have decided not to renew the contract of Argentine playmaker Emmanuel Ledesma as Aitor Karanka looks to target automatic promotion from the Championship.
Ledesma joins Dean Whitehead on the released list, with the former Stoke City midfielder being targeted by a host of Football League clubs after manager Karanka told him he couldn't guarantee him first team football.
Ledesma never truly convinced Boro fans
The 27-year-old joined Boro from Walsall in the summer of 2012 during current Coventry City manager Tony Mowbray's tenure at the club, but went on to make only 56 league appearances.
He scored eight goals in the Championship for the Teesside outfit, but only sporadically showed flashes of his ability and has spent time out on loan with Rotherham United and Brighton & Hove Albion in the last 12 months.
Indeed, he turned out for Boro just twice in their highly-successful 2014/15 season, his most recent appearance in the red-and-white shirt coming way back in September as Boro struggled to a draw against Blackpool under the floodlights.
A number of youth academy graduates have been released
Youth academy product Seb Hines, now 27, is another on the Boro released list as the club look toline their squad in what is expected to be a busy summer of transfer activity.
With Chelsea defender Tomáš Kalas set to re-join on loan, Hines has been deemed surplus to requirements at the Riverside Stadium, and has been told he can find a new club for himself.
Hines spent the second half of last season playing alongside former Ballon d'Or winner Kaká, as he agreed a six-month loan deal with Major League Soccer outfit Orlando City.
Jonathan Woodgate could still remain at the club
Meanwhile, Boro are still waiting on the decision of club stalwart Jonathan Woodgate as to whether he will remain on the playing staff.
The defender, formerly of Real Madrid and Leeds United, has been told he would be welcome on the club's coaching staff by his manager, but Karanka has also said he would "love" Woodgate to continue playing.
David Atkinson, James Warnett, Kieron Weledji and Ryan Brobbel have also been released by the club after failing to impress the first-team coaching staff sufficiently to earn extensions to their contracts.