Leeds face a £100m transfer deal if they fail to win promotion to the Premier League as a worrying omen emerges

2019 – HIS latest failure was one of the most dramatic and traumatic in the club’s history.

That season, Leeds – under Marcelo Bielsa – were caught red-handed sending spies to spy on Derby’s training during the regular season, in an incident famous as Spygate.

And it was written in the stars that the two clubs would face each other in the play-offs. Leeds were heading towards victory in the two-legged semi-final – winning 1-0 at Pride Park thanks to a Kemar Roofe goal and then winning 2-0 in the draw after Stuart Dallas had put them ahead at Elland Road.

But a remarkable second half saw Derby win 4-2 that night – with Manchester United midfielder Mason Mount among the scorers – to claim a 4-3 victory.

This prompted Rams boss Frank Lampard and his players to celebrate, miming using binoculars to mock their opponents for their spying antics.

2009 – LEEDS were in their second season of three in League One and finished fourth to reach the end of season lottery where they faced Millwall in the semi-finals.

And Neil Harris’s winner 19 minutes from time gave the Lions a lead heading into Elland Road for the second leg.

But Luciano Becchio gave the West Yorkshire faithful hope by giving his side the lead – only for it all to end in tears when midfielder Najim Abdou delivered the fatal blow for the south Londoners 16 minutes from time.

2008 – Having dropped down to Division Three for the first time in their history, Simon Grayson’s men were hopeful of recovering at the first attempt.

But they had to settle for the play offs after finishing fifth.

And they reached the final after coming from 2-0 down against Carlisle to win the two-legged semi-final 3-2 on aggregate.

But James Hayter dismissed Doncaster’s winner at Wembley to send Leeds’ Yorkshire neighbors into the Championship.

2006 – TWO seasons after abandoning the Premier League, Leeds were given the chance to bounce back after finishing fifth in the Championship.

They managed to reach the final after beating Preston 2-0 at Deepdale, with goals from Rob Hulse and Frazer Richardson sealing a 3-1 aggregate victory. But they didn’t make things easy for themselves as Stephen Crainey was sent off with 21 minutes remaining and Richard Cresswell followed in stoppage time.

But the final was a complete disaster, with Watford winning 3-0 at Wembley, with Jay Demerit and Darius Henderson, from the penalty spot, scoring after an own goal from goalkeeper Neil Sullivan.

1987 – LEEDS were involved in a play-off marathon at the time where both the semi-final and final were played over two legs and if the score was tied the match would be replayed at a neutral venue.

After overcoming Oldham in the semi-finals on the old “away goals rule”, they played the final home and away against Charlton.

Both teams won the home match 1-0 – James Melrose scored the winner at Selhurst Road, where the Addicks shared the ground, and Brendon Ormsby at Elland Road.

Therefore, the final had to be decided with a replay at St Andrew’s, Birmingham City.

And after a goalless draw after 90 minutes, the game went into extra-time and although John Sheridan gave Billy Bremner’s side a 99th-minute lead, Charlton prevailed with a late double from Peter Shirtliff.