The two east London outfits will face off at Wembley Stadium with Charlton looking to make a long-overdue return to the second tier.
The Addicks, under the stewardship of Nathan Jones, were relegated from the Championship in 2020 after just one season back at that level.
Meanwhile Orient, led by Richie Wellens, have never played in the Championship in their history, and promotion would add another chapter to their remarkable rise from recent adversity.
The club tumbled out of the Football League in 2017, ending a 117-year stay in the top four divisions of the pyramid as they wrestled with financial insecurity under the ownership of Francesco Becchetti.
The O’s won promotion back to League Two in 2019 under Justin Edinburgh, before Richie Wellens won them the fourth tier title in 2023.
The pair finished fifth and sixth respectively in the League One table, with Charlton defeating Wycombe in a tense 1-0 aggregate win, while Orient beat Stockport County on penalties to book their place in the Wembley showpiece.
Adds Up: Tyreece Campbell
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Date, kick-off time and venue
Charlton v Leyton Orient is scheduled for a 1.01pm BST kick-off on Sunday, May 25, 2025.
The match will take place at Wembley Stadium.
Where to watch Charlton vs Leyton Orient
TV channel: In the UK, the game will be televised live on Sky Sports Football, with coverage starting at 12pm BST.
Live stream: Sky Sports subscribers will be aim to stream the game live on Now TV.
Live blog: You can follow all the action on matchday via Standard Sport’s live blog, with expert analysis from Dom Smith at the ground.
Free highlights: The Sky Sports app and YouTube channel will show highlights of the game.
Orient express: Jack Currie
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Charlton vs Leyton Orient team news
Addicks fans can expect a full complement to traverse the city come Sunday, with no injury worries for Nathan Jones.
There may be a slight question mark over Luke Berry, who missed the second leg win over Wycombe with a minor injury, while Chuks Aneke returned to Jones’ matchday squad following a three-game suspension after his red card during the 4-0 win at Wycombe back in April.
As for Orient, Wellens will be without long-term absentees Dan Happe and Tom James, with the defenders ruled out for the season after being forced off in last month’s 0-0 draw with Wigan.
Otherwise, Wellens will a full squad to pick from as he looks to guide the O’s into the second tier for the first time.
Charlton vs Leyton Orient prediction
Orient were the form team going into the play-offs, winning their last six games to seal the final top-six spot.
Those wins included crucial victories against fellow play-off contenders Wycombe (1-0) and Huddersfield (4-1), which showed their mettle when the presure intensified.
They battled back from 2-1 down in the first leg of their semi-final against Stockport at Brisbane Road, before they held on at Edgeley Park to take County all the way to spot-kicks in a nervy second leg.
Charlie Kelman, who netted a brace in the first leg to supplement his 21 goals in the regular league season, will be pivotal to their chances of victory at Wembley, and momentum is with them going into Sunday.
As for Charlton, Jones’ side had to bounce back quickly after a 3-0 drubbing at Wrexham on the penultimate day of the campaign, beating Burton 3-1 in the final fixture to return to winning ways ahead of the play-offs.
Matt Godden’s experience came in handy as he notched the winner over two legs against Wycombe, and that could prove vital again here.
Head to head (h2h) history and results
The two teams first met in the old Third Division in 1993, with Charlton winning 3-1.
Since then, it’s been fairly even…
Charlton vs Leyton Orient match odds
Leyton Orient to win: 11/8
Odds via Betfair (subject to change).
