Middlesbrough have released Jonathan Woodgate, Damia Abella and Rhys Williams ahead of their return to the Premier League.
The out of contract players have not been offered new deals by Aitor Karanka as the club look to reshape their squad ahead of the 2016-17 campaign.
Defender Williams is set to return to Australia to join Perth Glory, with both Woodgate and Damia joining their fellow defender in departing the Riverside.
Former Newcastle United, Leeds United and Real Madrid centre-back Woodgate - who made 112 appearances for his hometown club - was restricted to just one appearance last season, against Burton Albion in the Capital One Cup.
It was originally announced that 36-year-old Woodgate would depart last summer, but in an eleventh-hour move he re-joined the squad midway through the pre-season training camp in Marbella and signed a one-year contract.
Meanwhile, injury completely wiped out Damia’s season with the Spaniard battling to recover from snapping his anterior cruciate ligament at Cardiff back in September 2014.
The 34-year-old made seven appearances in total, following his arrival two summers ago from Osasuna.
Officials at Boro have also confirmed three of the club's younger players have also departed; goalkeeper Luke Coddington, who has already agreed terms with Huddersfield Town, former Hartlepool United loanee Jordan Jones and full-back Andre Bennett, who has spent time on loan at Gateshead.
A club statement said: "The club like to place on record its thanks to all the players and wish them all the best for the future.
"In addition to the trio, loan players Tomas Kalas, Gaston Ramirez, Ritchie de Laet, Kike Sola and Michael Agazzi have also now officially returned to their parent clubs."
Chelsea defender Kalas made 47 appearances for the club in two loan spells - 26 in the Sky Bet Championship last season - while Ramirez featured 18 times last term, scoring seven goals, after joining from Southampton in January.
Both players have been linked with a return to the Riverside on a permanent basis after helping Boro win promotion back to the top flight after a seven-year stint in the Championship.
De Laet, meanwhile, joined from Premier League Leicester City in January and went on to make 10 appearances.
Kike Sola made just one start and one substitute appearance for the club after joining on loan from Athletic Bilbao at the start of the year.