Leyton Orient must be aware of Charlton Athletic completing heartbreaking hat-trick - it would be so cruel at Wembley | OneFootball

Leyton Orient will be eager to avoid another late defeat against their South London opponents.

Leyton Orient's incredible season will culminate at Wembley Stadium after reaching the League One play-off final.

The O's, following on from their semi-final victory over Stockport County, will now face South London side Charlton Athletic for a place in the second tier, a level Orient haven't played at since 1982.

However, recent history does not look kindly on the O's, as the Addicks got the better of them on both occasions in League One this year - and Orient will be desperate to avoid a third heartbreaking defeat so late into the season.

Late goals cost Orient dearly in previous fixtures

Back in August, the O's headed to the Valley following their opening day defeat at home to Bolton Wanderers. In a fixture that saw the Addicks on top for large periods of the game, it was a Luke Berry strike in added time that condemned Orient to their second defeat in two league games.

Both Orient and Charlton then proceeded to go on similar runs of falling towards the bottom end of the table, with Orient even dropping into the relegation zone in late November, before picking themselves up towards the end of 2024 and into the New Year. They even faced off in the Vertu Trophy in mid-December, with the O's picking up a 2-0 win courtesy of late goals from Dan Agyei and Charlie Kelman.

By the time the two London sides met once again, this time at Brisbane Road at the start of March, the expectations were much different from both sets of supporters who were dreaming of promotion.

A Jordan Brown strike from distance early in the second half looked to have been the deciding factor in the match, before goals from Macauley Gillesphey and Kayne Ramsay in added time gave the visitors the three points.

With both league fixtures ending in the same dramatic fashion, Orient fans will have a familiar worry that the infamously quoted "typical Leyton Orient" will creep in and their season will end in similar heartbreaking fashion.

Orient and Charlton set for blockbuster Wembley clash

While many neutrals have taken to social media to say that Stockport edged the O's in their tie, or that Charlton's semi-final tie against Wycombe Wanderers was poor from an entertainment standpoint.

Despite this, the fact is that throughout the grueling 46-game league season and the additional play-off games, both sides earned their place at the home of English football.

On paper, both teams seem to match up well, and for the most part some last-minute brilliance from the South Londoners has been the difference between the two.

However, play-off games are always special in the sense that all prior performances and form goes out the window - something Charlton fans will remember very well from their last win at Wembley, defeating Sunderland back in 2019 to gain promotion to the Championship despite failing to defeat them in either game during the season.

Both fans are right to have a sense of confidence based on their season so far, and while falling at the biggest stage would be cruel for either team, Orient should retain the memories of their previous gut-wrenching defeats against Charlton and keep it as a reminder to not collapse in the same way at the final hurdle.

At the end of this long season, it could be that the final place in next season's Championship is decided by the very last kick of a ball in League One. The late drama we've seen between Orient and Charlton indicates that's a very good bet.