Finding a way to lose: Why Sunderland are the undisputed kings of play-offs heartbreak

If you want to know just how painful the Football League play-offs can be, the best way to find out is by asking Sunderland fans.

The annual carnage of the Football League play-offs is nearly upon us, and the guaranteed heartbreak for someone always makes them compelling viewing for neutrals.

However, there is one club who excels at play-off heartbreak like no other.

Sunderland will face Sheffield Wednesday to decide who advances to the final at Wembley, and if any Black Cats fans are looking forward to it they probably haven't been paying enough attention.

The north-east club's history with these particular games is possibly unlike any other, and there can be little doubt that Sunderland are the undisputed kings of play-off heartbreak.

Here is a complete history of Sunderland and their play-offs involvement.

Gillingham 1987/87 - Relegated

Sunderland Gillingham Sunderland Echo

Play-offs with relegation as a consequence is quite common in Scotland and Germany, but the English leagues dispensed with them a long time ago. Of course, with fresh and juicy play-off heartbreak available, Sunderland made sure they were at the front of the queue.

It wasn't supposed to be like that for Sunderland. Around 18 months before they appeared to have pulled off a real coup by luring Lawrie McMenemy back to the north-east after his successes with Southampton. It was assumed that would all but guarantee promotion to the First Division, not relegation to the Third.

McMenemy was gone by the time that had happened, with the club attempting to replicate some of the 1973 magic by appointing Bob Stokoe as a caretaker manager.

He was unable to save them, and Sunderland being Sunderland they naturally chose the most heartbreaking way possible to lose.

They went to Third Division Gillingham for the first leg and lost 3-2, but most people fancied their chances at Roker Park. They did win it, and even scored a last-minute goal to force extra-time.

Momentum with Sunderland, you might be thinking? Not in the play-offs. They won the game 4-3 but lost on away goals and dropped into the third tier for the first time in their history.

Swindon Town 1989/90 - Lost the final, but…

Sunderland and Swindon in 1990 play-off final

Here's a quiz question for you: Who are the only team to get promoted via the play-offs who actually lost the final?

Even for a club with Sunderland's storied play-off history, 1990 was a bit of a crazy one. Sunderland finished sixth in the Division Two (now Championship) table and that meant playing the third-placed team, which of course was bitter rivals Newcastle United.

The first game at Roker Park was drawn 0-0, but Sunderland saw a last-minute penalty saved. The man who missed it, Paul Hardyman, took it pretty badly and kicked Magpies goalkeeper John Burridge in the head for saving it.

"I blocked it and the next thing I knew I felt my nose go," Burridge later recalled. "The funny thing is that I lived in Durham city, and Hardyman lived on the same estate.

"He was only round the corner, and I felt like going and putting his f***ing windows out."

Stuff only got weirder from there.

Sunderland won the second leg at St James' Park 2-0, but the game had to be suspended with five minutes left because unhappy Newcastle fans invaded the pitch en-masse to try and force the game to be abandoned and replayed.

It wasn't, of course and Sunderland went on to the final at Wembley. They lost it 1-0 to Swindon courtesy of an own goal, but that was not the end of the story.

Swindon were later found guilty of making illegal payments to players and someone had to take their place. Newcastle said it should be them because they finished third. Ron Atkinson, the Sheffield Wednesday manager, believed his relegated team should be allowed to stay in the First Division. Swindon thought it should still be them.

It seemed very few people at all thought it should, or would, be Sunderland, except the Football League, and the Wearsiders were promoted. Some might say, and history may support this, that Sunderland used up all of their play-off good luck in one fell swoop that year.

Charlton Athletic 1997/98 - Lost final on penalties

"The Charlton play-off final in 1998 is still the most painful memory I have as a football fan," recalls Sunderland fan Lynsey Thompson.

"I still can't watch or even think about that match without reliving the ultimate despair I felt as that last penalty was missed by a Sunderland home-grown hero.

Sunderland play-off Charlton 1998

"I still remember standing at Wembley, decked from head to toe in red and white, tears streaming down my face, feeling like I'd just gone nine rounds in a boxing ring, heartbroken, emotionally exhausted and vowing to hate Charlton for the rest of my days.

"I still remember the song that was played that day as we exited Wembley and still turn it off if it comes on the radio. Twenty-four years is still too soon."

The fact is that the Sunderland vs Charlton play-off final of 1998 is the stuff of legend. Ask most fans to name a play-off game and, aside from those involving their own team, it is likely the one they will mention.

Sunderland had been relegated the year before and had taken time to adjust to their new surroundings at the Stadium of Light. Once they got their act together, though, they were a brilliant team to watch and boasted a front two, Kevin Phillips and Niall Quinn, that would soon become the envy of most Premier League clubs.

Peter Reid's men had lost the semi-final first leg at Sheffield United but were able to turn it around at home and headed to Wembley favourites.

In the final they were losing at half-time, led three times, conceded an 85th-minute equaliser, then lost on penalties in sudden death after a 4-4 draw.

For the neutral it was a feast of footballing drama never to be forgotten. For Sunderland, it was a heartbreak never to be healed.

The Charlton hat-trick hero that day was Sunderland-born Black Cats fan Clive Mendonca. Of course it was.

Crystal Palace 2003/04 - Lost semi-final on penalties

Sunderland play-offs disappointment Crystal Palace

Sunderland were back in the play-offs a few years later, and the 4-4 scoreline would haunt them once more.

In fairness, Sunderland making it to the play-offs at all was a mini miracle. They had been relegated the year before in an absolutely desperate state, both in terms of football and finances.

They had to practically give away any even remotely desired player just to keep themselves afloat, yet managed to rally to a third-placed finish in the Championship.

Crystal Palace were to be the opposition. The first leg was lost 3-2, but it was far from a lost cause.

Of course, Sunderland then did what Sunderland do. Kevin Kyle and Marcus Stewart had the Black Cats 2-0 up and going through until the 90th minute, when Darren Powell levelled things up at 4-4 on aggregate.

Extra-time could not separate them, so penalties had to. John Oster, Jason McAteer and Jeff Whitley all missed, with the latter's proving decisive in sudden death.

Charlton Athletic 2018/19 - Lost the final in last minute

George Honeyman and Lynden Gooch dejected for Sunderland after play-offs defeat to Charlton

Charlton. Them. It had been 21 years since the Addicks broke Sunderland hearts at Wembley and the two sides were to meet again in the League One play-offs.

For any other club, this was a chance for revenge, to exorcise old demons, to put the record straight and end the hurt. For Sunderland, it was a chance to explore whole new ways to serve up fresh play-off heartbreak.

That was no mean feat, to be fair. The first play-off final between these two sides appeared to have it all so coming up with something original was going to be tough.

Sunderland had earned their ticket to Wembley by beating Portsmouth in the semi-finals. The first leg was a bad-tempered affair at Fratton Park but an uncharacteristically solid play-off performance from Sunderland saw them emerge with a goalless draw, despite some altercations between Black Cats players and home fans.

They won the home leg 1-0 and Charlton awaited them at Wembley. It was a new Wembley, though, and a new Charlton, but it was the same old Sunderland.

With the game moving into the dying stages at one goal apiece, it seemed for all the world like extra-time was looming again.

As usual where Sunderland and play-offs are concerned, things were nowhere near what they seemed to be, and Patrick Bauer scored a Charlton winner in the fourth minute of injury time.

Lincoln City 2020/21 - Lost in semi-final

Sunderland play-off Lincoln

For any other club, this one might have felt quite unlucky. For Sunderland it felt like quite a pedestrian play-off exit.

The season had been played behind closed doors due to Covid-19, but restrictions had lifted a little for the play-offs. Each team were allowed a reduced number of home fans, although away supporters were not permitted.

That made for energetic crowds and frantic matches, and Sunderland struggled with that at the LNER Stadium. They lost it 2-0, with the second coming from a charged down clearance from their goalkeeper.

It was Sunderland who had the crowd advantage in the second leg, and they looked like they were making the most of it. By half-time they had levelled the tie. It should have been even better, but Charlie Wyke somehow managed to miss an open goal after he rounded the goalkeeper.

Refreshed by that miss, Lincoln came out fighting in the second half and were able to get the goal they needed to ensure yet another year of play-off misery for Sunderland.

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