It's fair to say that Bolton have had more of an eventful time than most over the past few decades. 

The Trotters climbed from the fourth division in the late 1980s, flirted with the top flight in the 90s before establishing themselves as a Premier League stalwart in the 2000s.

In recent years, they have been on a downward trajectory and now look set for relegation to League Two this term.

That rollercoaster ride has included more a few woeful signings and with that in mind, we've compiled a list of six of the worst...

The Brazillian had starred in Turkey and Portugal prior to his arrival in the North West, scoring shedloads of goals, but he always seemed past it for the Trotters.

His time at the club would last just six months as he left to join Italian side Ancona in January 2004.

The arrival of the Spaniard from Atletico Madrid looked like it could be another Sam Allardyce masterstroke in the 2003/04 campaign.

That's not how it proved, however, as he failed to score in any of his 10 games for the Trotters and returned to Spain that summer.

Rasiak arrived as a potential replacement for Nicolas Anelka in 2007 and perhaps it is that comparison that has landed him on this list.

However, it could also be the fact that he made just seven appearances for the club and failed to score once.

Bolton beat out a number of other Premier League sides to sign a 20-year-old Sordell for around £4 million in January 2012.

It seemed the striker was destined for great things but it was not to be. The Englishman made only 29 appearances for the Trotters, scoring eight times, before he was moved on.

Casado's arrival in January 2016 was a relatively exciting one.

A product of the Barcelona academy, the defender had more than 100 La Liga appearances under his belt a the time but he proved an underwhelming acquisition – making nine appearances and being released after just five months.