Nine play-off appearances and five promotions: former Leeds United boss Simon Grayson on how to survive the end-of-season knockouts

Leeds United are one of those teams and Grayson oversaw their most recent failure when Millwall survived the heat of Elland Road to knock Leeds out in the League One semi-finals in 2009. There is a consistent thread when United reach the play-offs: of defeat following defeat and United’s complex about them growing. Marcelo Bielsa’s first attempt to master them is an attempt to break a record which “has to end sometime”, according to an optimistic Grayson.

Grayson would know. He was the coach who led Preston North End to water in the League One final in 2015, their first promotion via the play-offs at the 10th time of trying and a result which redressed the worst record in the EFL. Leeds have four play-off losses behind them, the first in 1987 and the last on Grayson’s watch, and Millwall’s progression after a 1-1 draw at Elland Road 10 years ago is his best example of how quickly a two-legged tie can turn.

Leeds were 1-0 up on the night and level at 1-1 on aggregate after Luciano Becchio’s goal ignited Elland Road and left Millwall on the ropes. Then came a lengthy delay as Millwall defender Zak Whitbread received treatment on a head injury and Leeds’ weight of pressure was gone. Jimmy Abdou scored with a sweeping, close-range finish to eliminate a United squad who, prior to the play-offs, had won nine of their last 11 league games.

“We had Elland Road rocking after Lucanio scored and everybody in the ground was thinking ‘only one team will win this now’, including me,” Grayson said. “But the break for that injury broke our flow and took the wind from our sails a bit. It was a lifeline for Millwall at a time when they needed it. I’m sure it was a genuine injury; you go from piling on the pressure to kicking your heels and standing around for four or five minutes. The atmosphere drops.

“That’s the thing about the play-offs. You need to play well and you need to keep to the game plan that’s worked for you but even with all that, there are going to be little moments that go for or against you and they can be crucial. It’s a different mindset too because it’s you or them and results elsewhere don’t help. There’s massive pressure in the play-offs but I’ve always loved them.”

Bielsa is about to find out how much they appeal to him. Leeds will contest the first leg of their semi-final a week on Saturday, away from home against whichever side finishes sixth. There will be an unavoidable thought amongst his players that their season should already be finished, with automatic promotion confirmed, but Grayson saw the same situation at Preston.

North End had second place in League One in their hands but finished third after losing to Colchester United on the final day. Victory would have taken them up.

“You can’t hide the disappointment of that but I tried to make the players see the positives,” Grayson said. “All I said to them was ‘we’ve got a second chance to get it right. You were second and you’ve finished third but, if we were sixth and finished seventh, we’d be done and dusted and you’d all be on the beach. So think of that as a good thing.’ Once you get your head around the situation, and this is probably the same from Leeds’ perspective, you start to think about what could still happen.

“I tend to look at it positively anyway because the play-offs are brilliant. I won twice and lost twice as a player and I’ve lost twice and won three play-off finals as a manager. If someone could guarantee you victory at Wembley then I’d take that over automatic promotion every time because of the experience of the day itself but losing there really hurts. It’s a horrible moment. So really, I’d take second place and automatic all day long.”

Leeds, under Billy Bremner, were seven minutes from winning the Division Two play-off final in 1987, only to concede twice to Charlton Athletic in extra-time. The club were routed by Watford in the Championship play-off final in 2006, offered little in a 1-0 defeat to Doncaster Rovers in the League One final two years later and failed to navigate their way past Millwall over two legs on Grayson’s watch. This will be their fifth attempt to master the EFL’s knockouts.

“We had the same thing at Preston,” Grayson said. “Preston’s record was the worst of anybody’s and, before the final against Swindon (in 2015), you could sense people thinking ‘no chance’. On the outside it was that feeling of ‘we won’t win it because we never win the play-offs’. But records are there to be broken and records are often irrelevant. Usually you’re talking about different managers, different players, different eras and different opponents so the fact that Leeds didn’t do it 10 years ago or 20 years ago has no bearing on anything. In a way it might help them because a record like that has to end sometime, just like it did for Preston.

“The one thing that really pleased me against Millwall was the way we fed off the crowd at Elland Road. We weren’t nervous about it and we didn’t let the expectation worry us. It just didn’t go our way on the night. A big part of getting out of the play-offs is allowing yourself to enjoy them, even with all the pressure you’re under.”

United’s board have already started planning for two eventualities: a season in the Premier League or the more sobering reality of a 16th straight year in the EFL. The club want Bielsa to remain in charge as head coach regardless and are hopeful that he will but they will not be able to press the button on any strategy until the play-offs are over.

“You do lose two or three weeks when you could otherwise be planning for the division above,” Grayson said. “The play-offs delay your preparation and they don’t make it easier for the season that’s coming but once your in them, all of that thinking goes out the window for a manager. Whatever’s happened, deep down your happy that you’re still in with a chance.”