Nottingham Forest's Player of the Year once left for nothing - he's still playing at 39 | OneFootball

Garath McCleary left Nottingham Forest for free after winning the fans' player of the year. Aged 39, he's still playing in the EFL

There aren't many non-league players who impress enough to be offered an immediate move to the Championship, but that was the case with Garath McCleary in 2008.

The Oxford-born wideman began his career at Oxford City before moving to Slough Town and then Bromley, making over 70 league appearances in four years across all three sides before his talents piqued the interest of Nottingham Forest boss Colin Calderwood.

After a successful trial period, the then-20-year-old McCleary moved to the City Ground and turned professional, kickstarting a career which has spanned well over 600 games in all competitions alongside representing Jamaica 24 times.

And while it's been over 18 years since his pro debut back in March 2008 in a 1-0 loss to Carlisle United for Forest, the 39-year-old is still playing regularly in League Two.

How Garath McCleary won Nottingham Forest Player of the Year, despite playing just half a season

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Following his first full campaign, where he missed just seven league outings, McCleary struggled to stay fit for long periods during his time at the City Ground, making just 24 and 18 Championship appearances respectively in the following two years.

He began the 2011/12 term on the shelf, too, watching from the sidelines as Forest struggled towards the foot of the second tier table.

McCleary came back in December, but was unable to immediately turn the form around, and a run of one win in 13 actually saw them prop up the division in mid-May. It was from that point that the winger kicked into gear.

In the next seven games, Forest won four times, culminating in that famous 7-3 win against Leeds United at Elland Road in March 2012. McCleary netted four in that one, taking his tally then to nine with two assists in 17 league games.

He assisted a few more goals in wins over Crystal Palace and Peterborough United, and actually got sent off in the latter two. He returned on the final day to assist in a 2-0 win over Portsmouth, as Forest finished 19th.

Despite only making 22 league appearances that year, his 15 goal contributions earned him the club's Player of the Year, beating Joel Lynch and Chris Gunter to the award.

Garath McCleary would leave Nottingham Forest for free that summer

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But whether it was due to injuries or the fact that McCleary wasn't much of an important first-teamer before that surge in form in 2011/12, his contract was out at the end of that campaign.

Forest, understandably, offered him a new deal, but the then-25-year-old opted for a move to Reading instead, who won the Championship that season and were looking to re-establish themselves in the Premier League.

It would definitely have frustrated Forest fans at the time, but ultimately, they shouldn't have let his contract run down. For McCleary, he'd gone from non-league to the Premier League in the space of five years.

His time in the top flight only lasted one year, with the Royals immediately suffering relegation, but he ended the year with three league goals.

Garath McCleary would become a Reading, and then Wycombe Wanderers, stalwart

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Looking back, McCleary is arguably one of the best free transfers in Reading's history. The wideman didn't immediately look for a route out of the Madejski Stadium, instead staying and trying to help the club back into the top flight.

The Royals haven't been in the Premier League since that 2012/13 campaign, enduring some tumultuous seasons in the second tier, all with McCleary at the club.

Indeed, the winger scored five and assisted 11 in their first year back in the Championship, as they finished seventh under Nigel Adkins and Steve Clarke. He also scored nine and assisted nine a few years later, helping Reading finish third under Jaap Staam.

Outside of that, he's been at the club through relegation battles and consecutive 20th-place finishes before leaving in 2020, having made 270 appearances in all competitions for the Royals across eight years of service.

In 2020, McCleary was 33 and joined up with Wycombe Wanderers on a one-year deal to provide some experience for a Chairboys side in the Championship for the first time ever.

He didn't end up being any ordinary veteran signing, though, as while Wycombe were relegated back to League One immediately, McCleary stayed until he was 38, and his 219 appearances at the time ranked him 14th in all-time league appearances for the club.

The aged winger wasn't just being carried along by his teammates, either. He was a key part of some promotion-chasing League One sides at Adams Park, registering 18 goal contributions in 2021/22 en route to a play-off final defeat against Sunderland and 10 in the 2024/25 term as the Chairboys battled with Birmingham City and Wrexham atop the third tier.

Garath McCleary isn't done with his professional career just yet, singing for Gillingham in 2025

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Aged 38 and with well over 500 appearances across both the Championship and League One, you wouldn't put it past McCleary to hang up his boots last summer.

However, he reunited with former Wycombe boss Gareth Ainsworth at Gillingham, signing a one-year deal with the League Two side with an option of a further year, which the Gills have ended up taking.

Last season, McCleary managed 27 fourth-tier games, scored four times and assisted a further six. As of writing, this year, he's been in squads throughout the infancy of the term, but is yet to start a league game.

At 39, he's the third-oldest player in League Two, with Rochdale legend Ian Henderson coming to take the mantle, as he turns 42 in January.

And if Gillingham can have a good season and sneak into the top seven, McCleary could see himself playing EFL play-off football in his forties, with the 2026/27 campaign set to end one week before his 40th birthday.