The attacking midfielder, who has been a supporter of the Black Cats since childhood and is from County Durham, left Peterborough United following the expiration of his contract back in 2020
A half-season loan spell at Hull City failed to result in a permanent move before Maddison had stints at Charlton Athletic, Bolton Wanderers and Spalding United and even took some time away from the game.
The 28-year-old was frequently linked with Sunderland since their relegation to League One, but it is thought that he was never actually a genuine target for Jack Ross, Phil Parkinson or Lee Johnson.
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In February this year, Maddison set up a GoFundMe in an attempt to fund surgery in the hopes it would help him continue playing following a career-threatening injury. He reached the target in less than 24 hours.
Now, Maddison has signed with Darlington, who play their football in the Vanarama National League North.