5. Kevin Nicholls
Leeds’ gritty 2006-07 season saw them relegated to League One, with the Kevin Nicholls saga one of several uninspiring subplots.
Kevin Nicholls arrived from Luton in the summer of 2006 for £700,000. He injured knee ligaments in his first training session. Another injury soon followed which kept him out until December.
During that lay-off Dennis Wise had made the midfielder captain, only for him to demand a transfer back to Luton by March. Wise dug his feet in, demanding Luton match the fee that Leeds paid for him, only for Preston to come in and cough up.
4. Roque Junior
Roque Junior was signed on loan from AC Milan in 2003 having helped Brazil win the World Cup just 12 months previously. He prompted great excitement when he arrived at Elland Road.
But was followed was a disastrous debut against Leicester City. The Whites conceded 24 times in his seven appearances on their way to relegation from the Premier League, making him worst Leeds United signings ever.
3. Paul Rachubka
Rachubka was signed as a back-up to Andy Lonergan in 2011. He was forced into action after the Leeds No.1 picked up an injury early in the season.
For a certain generation of Leeds United fans, it will perhaps go down as the worst individual performance in Ellland Road history.
Back in November 2011, Leeds went into the half-time dressing room 3-0 down to Blackpool, with Paul Rachubka at fault for all three goals.
He didn’t come out for the second half. Or ever put on a Leeds shirt again. All of this was enough for him to earn a place in worst Leeds United signings ever.