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Charlton Athletic’s last League One play-off final win came courtesy of a legendary late winner after ‘freak’ goal

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Charlton Athletic face Leyton Orient in the 2024/25 League One play-off final on Sunday.

Charlton Athletic are preparing to take on Leyton Orient in the 2024/25 League One play-off final for a place in the Championship next season.

Head coach Nathan Jones has masterminded the Addicks’ fourth-placed finish this term, with his side beating Wycombe Wanderers 1-0 on aggregate across the two semi-final legs.

Richie Wellens’ Leyton Orient side, who beat Stockport County 4-1 on penalties to reach the final showpiece, have been one of the third tier’s most potent attacking sides with league top goalscorer Charlie Kelman spearheading their attack.

Addicks boss Jones will be hoping that Charlton’s history, from their last League One play-off final win, is repeated on Sunday afternoon.

Charlton Athletic v Sunderland - Sky Bet League One Play-off Final
Photo by James Chance/Getty Images

Charlton Athletic’s last League One play-off final win came against Sunderland

Charlton’s last League One play-off final win came against Sunderland in the 2018/19 showpiece under Lee Bowyer.

Bowyer’s side ended the regular campaign in third, three points adrift of automatic promotion, as the Black Cats finished in fifth.

Jack Ross’ Black Cats dominated the opening exchanges under the Wembley arch, and with five minutes on the clock came one of the biggest blunders ever made in a play-off final, to put Sunderland one goal ahead early on.

Naby Sarr’s back pass, under no pressure, was missed by Addicks goalkeeper Dillon Phillips to gift Sunderland the lead in embarrassing fashion.

However, the duo’s blushes were spared thanks to an equaliser from Ben Purrington and an injury-time winner courtesy of Patrick Bauer, to leave Sunderland crestfallen at Wembley.

Via Football.London, Bowyer said of the final: “There’s things that you can’t control. We couldn’t control that it’s just one of those freak things that happens in the game, but it just showed our character and togetherness to come together and score.

“I’m just proud of everyone, and it’s probably the proudest moment of my whole career. I’m just delighted for this football club.”

That clash between Charlton and Sunderland was the latest in the lineage of dramatic play-off bouts between the two sides.

In the 1997/98 Championship play-off final, dubbed the “greatest play-off final ever”, Charlton beat Sunderland 7-6 on penalties after extra-time ended 4-4.

Being victors in the best Championship play-off final ever, and coming from behind to win in their most recent play-off final outing, provides positive omens for Jones’ Addicks side ahead of Sunday’s showpiece.

Nathan Jones, manager of Charlton Athletic, celebrates victory
Photo by Andrew Redington/Getty Images

Can Charlton Athletic repeat play-off success in final vs Leyton Orient

Charlton Athletic headed into the play-offs with a projected 26.6 percent chance of winning the final, as per the OPTA supercomputer predictions.

Defensive midfielder Conor Coventry will be key for Charlton to secure the League One play-off final victory after his impressive campaign in the Addicks’ engine room.

Charlton are attacking much better to end the campaign, whilst maintaining their resolute defensive structure set out by head coach Jones, which could win Jones promotion.

Orient’s attacking threats include League One’s top goalscorer Charlie Kelman, and top assist-maker Jamie Donley, who promise to be a handful for the Charlton backline to contend with.

History in the League One play-off final after their Black Cats victory points in Charlton’s favour, as does their head-to-head record against Orient this term.

Charlton have taken maximum points in the league against Orient this term, winning 1-0 at home in August and 2-1 on the road in March, which will fill Jones’ squad with confidence ahead of Sunday’s season-defining bout.