A potted history of Leeds United’s play-off heartbreak: Southampton added to the list…

Leeds United were unable to exorcise their play-off demons after losing to Southampton in the 2024 Championship play-off final.

Daniel Farke’s side finished third in the Championship – the first side since Sunderland in 1997-98 to hit 90 points and not get automatically promoted – but thrashing Norwich City in the semis raised hopes of promotion. Alas, the Whites lost to the Saints at Wembley.

We’ve taken a closer look at Leeds’ disastrous play-off record over the years, having never made it through in five previous attempts.

1986-87: Charlton Athletic

Prior to their fall from grace in the mid-noughties, Leeds had an earlier wilderness period, dwindling in the old Second Division from 1982 to 1990.

The legendary Billy Bremner returned to Elland Road as manager in 1985, tasked with taking the club back to the promised land.

A third successive season of midtable mediocrity resulted in a wholesale revamp of the playing squad and a massive leap forward in 1986-87, in which Leeds finished fourth and enjoyed a memorable run to the FA Cup semi-finals, where they lost to shock winners Coventry City.

The fourth-place finish was enough for Leeds to make it into the inaugural play-offs – where they made it past Oldham on away goals, Keith Edwards scoring in the dying minutes of both legs.

Standing in their way of a return to the top flight were Lennie Lawrence’s Charlton Athletic, who had finished 19th in the First Division – things were different then, and it was played over two legs as opposed to a one-off at Wembley.

Leeds lost 1-0 at Selhurst Park before levelling the tie, via Brendon Ormsby, at Elland Road. The result? A hastily arranged replay ‘third leg’ (we told you things were different back then) at St. Andrew’s.

Goalless over 90 minutes, Leeds went ahead through John Sheridan in extra time – only for Peter Shirtliff to respond with goals in the 113th and 117th minutes for Charlton. An epic that ultimately ended in heartbreak, setting the tone for Leeds’ future play-off endeavours.

QUIZ: Can you name the clubs these 20 former Leeds United stars are playing for in 2024?

2005-06: Watford

It’s largely forgotten now, given that Leeds subsequently dropped into the third tier for three seasons and ultimately took 16 years to make it back to the Premier League.

But “Doing a Leeds” would never have entered the footballing lexicon, with its own Wikipedia page and everything, had they managed to bounce back after just two seasons.

With Ken Bates as chairman and Kevin Blackwell as manager, Leeds weren’t exactly right as rain in 2005-06, their second season in the newly-rebranded Championship. But they were functional enough to comfortably finish in the play-offs, albeit in terrible form with one win in 10 to see out the regular season.

In the semis, Preston took a 1-1 draw away from Elland Road, prompting Billy Davies to write “Job Done” in the away dressing room, their triumphalism fueling Leeds’ highly charged performance in the second leg – a 2-0 victory at Deepdale.

Blackwell’s Whites couldn’t reproduce anything like that display come the final, against Aidy Boothroyd’s Watford, at the Millennium Stadium. They were limply defeated 3-0 – a scoreline that underlined that side were nowhere near ready for the Premier League, on and off the pitch. The following season, Leeds finished rock bottom of the Championship after a 10-point deduction for entering administration. Now that’s doing a Leeds.

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2007-08: Doncaster Rovers

Beleaguered Leeds’ woes did not end with the 10-point penalty the season before. That summer they became the first club since Barnet in 1993 to be put up for an expulsion vote. The club retained their Football League status but were docked 15 points to rub extra salt into the wounds of their first-ever season in the third tier.

After a dodgy pre-season, Leeds started the campaign in a defiant mood, scrubbing away the -15 by winning their first seven matches, shooting up the table after dropping just four points from the first 39 available.

But they couldn’t quite sustain those results and a major mid-season wobble amid changes in the dugout (Gary McAllister replaced Dennis Wise) resulted in Leeds eventually finishing fifth – with a record that was comfortably top two.

Leeds lost 2-1 at home to Carlisle United in the first leg before a 2-0 victory at Brunton Park, courtesy of a brace from emerging academy graduate Jonny Howson – the tie-winner, struck from outside the box, sparked some of the wildest scenes of celebration ever seen in a Leeds away end.

But in Leeds’ first and as yet only appearance at the new Wembley, a Yorkshire derby against Doncaster, they once again failed to show up, losing 1-0 in a tight and largely cagey final.

It’s the 15th of May in 2008 and Jonny Howson scores twice to help #lufc beat Carlisle United in dramatic play-off fashion.

Some away day for the travelling Leeds fans 😍 pic.twitter.com/PYnrxRUFdF

— I'd Radebe Leeds (@Radebe_Leeds) May 15, 2024

2008-09: Millwall

There had been some promising signs during Gary Mac’s tenure, and Leeds possessed a squad that featured Fabian Delph, Jermaine Beckford, Luciano Becchio, Robert Snodgrass, Jonny Howson and Bradley Johnson – all of whom would go on to play in the Premier League (for other clubs).

But a shocking run of eight defeats from 13, and four in a row prior to Christmas, resulted in McAllister losing his job – while extinguishing any hopes of top two.

Things picked up considerably in the second half of the season under Simon Grayson. They rose to fourth, just five points off automatic promotion, and for once went into the play-offs as the form team.

Fat lot of good proved “momentum”. Grayson’s Whites lost 1-0 to Millwall at The Den before levelling the tie at Elland Road; Becchio making sure Beckford’s missed penalty blushes were spared. But in the 75th minute, Djimi Adbou emerged to equalise on the night, win the tie on aggregate and send Millwall to Wembley at Leeds’ expense.

The following season Leeds made it up automatically, but only in the most dramatic of circumstances, coming from behind with 10 men on the final day against Bristol Rovers. Elland Road had held its breath; every fan in the stadium knew what fate awaited them had they made it to the play-offs for a third successive year in League One.

READ: ‘F*ck it, I’m getting stuck in’: An oral history of Leeds 2-1 Bristol Rovers, 2010

2018-19: Derby County

There had been a couple of notable close shaves with the play-0ffs, but prior to Marcelo Bielsa’s arrival Leeds had settled into a deep second-tier malaise. Eight successive seasons finishing somewhere between 7th and 15th, but invariably a considerable distance off in the bottom half.

Everything changed from the minute the Argentinian tactician walked through the door and changed the culture at Elland Road. Leeds went from a side that had finished 13th, going nowhere under Paul Heckingbottom, to one that challenged the top end of the table while producing scintillating attacking football.

A drop in form saw Leeds end up behind Norwich City and Sheffield United in a thrilling three-way promotion race. Their play-off semi-final opponents were inevitably Derby County, who they’d comfortably beaten twice in the regular season, with the ‘Spygate’ scandal adding some extra spice with Frank Lampard.

Bielsa’s men shook off their late-season hangover to produce a third convincing victory over Lampard’s Rams, taking 1-0 back to Elland Road – before taking a two-goal aggregate lead via Stuart Dallas midway through the first half.

But anxiety from the stands seemed to envelope the players after a defensive mix-up between Liam Cooper and Kiko Casilla allowed the visitors back into it. By the hour mark Leeds were somehow behind in the tie. Leeds rallied to equalise via Dallas, but on a night that called for cool heads, fan favourite Gaetano Berardi lost his, was sent off late on, and Derby made the man advantage count to win 4-2.

The Athletic reported that Derby left a “dubious brown substance” in the away dressing room before racking up a £2800 bar tab in Leeds that night. They lost to Aston Villa at Wembley, while the following season Leeds ended up celebrating their promotion at Pride Park. All’s well that ends well?