10. Paris Saint-Germain (2011/12 - 107 million euros
Pastore, Gameiro, Menez and Matuidi all arrived in Paris in the summer of 2011, but they didn't bring trophies with them. This was the first season where PSG had Qatari backing, but it took the new owners a few years to bring success to the club.
9. Chelsea (2010/11) 121 million euros
The London club broke the bank in summer, but didn't manage a single trophy in the 2010/11 season. For Fernando Torres and David Luiz alone, Roman Abramovich parted with €85mill.
8. Tottenham (2008/09) - 142.5 million euros
The London side looked to reward Juande Ramos' good work as 'Spurs' boss by handing the manager the chequebook. They brought in Modric, Dos Santos, Pavluychenko, Wilson Palacios and Robbie Keane. Nearly 150 million euros that brought them nothing.
7. Valencia (2015/16) 143.7 million euros
The Spanish club earned its place in this list after Peter Lim's arrival. The figure is deceptive, however, as it includes signings from the previous summer whose fees were paid a year late. The spree brought in Rodrigo, Andre Gomes, Negredo, Santi Mina and Abdennour.
6. Manchester City (2008/09) - 147 million euros
Adebayor, Kolo Toure and Carlos Tevez all arrived in Manchester this summer, during the second year of the Abu Dhabi United Group's reign. It was the first full summer the new owners had to stamp their mark, but they weren't able to turn money into trophies.
5. Inter Milan (2016/7) - 158 million euros
After a poor period for the once dominant Italian side, the Chinese Suning group took over the club and brought a raft of new players in. Joao Mario, Gabriel Barbosa, Miranda and Candreva, among others, came to the 'Nerazzurro', but weren't able to return the club to glory.
4. AS Monaco (2013/14) 160 million euros
After being promoted to Ligue 1, Monaco spent the second largest amount of money out of any club in the French top tier in the summer of 2013. Falcao, James Rodriguez, and Joao Moutinho all moved to the principality, but PSG proved too hard to beat to the trophies.
3. Manchester United (2014/15) -195 million euros
Van Gaal landed in Manchester with the job of returning United to the successes of the Ferguson days. The club backed him with 200 million euros, incorporating Blind, Di Maria, Luke Shaw, Marcos Rojo and Falcao, but the only trophies they won were in their dreams.
2. Manchester City (2016/17) - 213 million euros
Pep Guardiola's first year with the 'Citizens' was a tricky one. Despite the club's heavy investment, with Stones, Sane, Jesus and Gundogan all coming in, Pep wasn't able to impose his winning ways straight away.
1. Real Madrid (2009/10) - 256 million euros
Cristiano Ronaldo, Benzema and Kaka. Florentino Perez broke the bank in 2009 in order to overtake Pep Guardiola's Barcelona. But it took Madrid more than a year to compete with the Catalan club and see the fruits of their investment, which holds the top spot in our list of unsuccessful spending.