Leyton Orient are reportedly in talks to sign free agent winger Owen Dale after he rejected the chance to stay with Plymouth Argyle.
The 27-year-old is available following the expiry of his contract with Oxford United, who were relegated from the Championship last season. Dale spent the 2025/26 campaign on loan at Plymouth, where he became a regular under Tom Cleverley during the second half of the season.
Plymouth had held talks over keeping Dale at Home Park on a permanent basis, but that route is now said to have fallen through. According to reports, Leyton Orient are discussing a possible deal with the winger, although his wage demands could become an issue in negotiations.
Dale joined Plymouth at the start of September, arriving after the summer transfer window had closed. He went on to make 32 appearances in all competitions, starting 25 of those matches, and became a regular option on the left side of midfield in Cleverley’s 4-4-2 system.
The Pilgrims had been keen to explore a return, with Cleverley making it clear in recent weeks that he would be open to bringing Dale back. However, the former Crewe Alexandra, Blackpool and Oxford winger now appears to be weighing up a move elsewhere as he assesses his options before the new campaign.
EFL experience
Dale would bring plenty of experience to Orient’s attacking department. He has spent the bulk of his senior career in the EFL, first emerging at Crewe before moving to Blackpool in 2021. He later had loan spells with Portsmouth and Oxford before joining Oxford permanently.
His time at Oxford ended this summer following their relegation from the Championship, with Dale becoming one of a number of players available in the free agent market. That has opened the door for clubs looking to add proven lower-league quality without paying a transfer fee.
Orient are said to be optimistic about the possibility of reaching an agreement, but there is still work to do. Dale’s wage expectations are reportedly a potential stumbling block, which could leave the deal dependent on whether the two parties can find common ground.
The situation also leaves Plymouth searching for an alternative after missing out on a player who already knew the squad and the manager’s system. Dale had been a useful part of their successful run in the second half of the season, but Argyle now look set to move on.
For Orient, this would be a notable free agent addition if they can get it done. Dale has League One experience, Championship exposure and a strong recent loan spell behind him, but the financial terms may ultimately decide whether talks become a completed deal.
