Barcelona (AFP) – Barcelona, the second richest football club in the world after Real Madrid, has been tainted by a series of legal woes in recent years involving its players and management.

Here is a recap of the most significant cases:

– Messi –

Under investigation since 2013 for tax fraud, the club’s Argentine striker Lionel Messi and his father Jorge Horacio were sentenced to 21 months in prison and slapped with a fine of 3.7 million euros ($4.1 million).

A Barcelona court found them guilty of using companies in Belize, Britain, Switzerland and Uruguay to avoid paying taxes on 4.16 million euros of Messi’s income earned from his image rights from 2007-09.

– Neymar I –

Barcelona’s signing of Brazilian striker Neymar from Santos in 2013 turned into a huge headache for the Catalan club. The following year Barcelona and its two previous presidents were charged with tax fraud over the deal.

The club said the operation cost 57.1 million euros but it had some contracts signed on the side with Santos which when taken into account would lift the price tag to 83.8 million euros.

Of this money 40 million euros were paid directly to Neymar as part of the transfer. Prosecutors deemed this money were part of his salary and should be taxed as such.

Barcelona in June reached an agreement with prosecutors to pay a fine of 5.5 million euros over the affair in a deal that sees the club avoid a tax evasion trial.

– Neymar II –

Neymar’s signing also sparked a dispute with Brazilian fund DIS, which owned part of the player’s image rights before he joined Barcelona. The club feels cheated by the deal and filed a complaint against Barcelona, Santos, Neymar and his father.

A Madrid court is investigating the case. Prosecutors have asked that Neymar and his father be tried for corruption and that the two clubs and their former management be tried for embezzlement.

– Mascherano –

Messi’s Barcelona and Argentina teammate Javier Mascherano was sentenced in December to a one-year suspended sentence for tax fraud after he was found guilty of failing to pay 1.5 million in taxes for 2011 and 2012.

Unlike Messi he avoided trial by admitting to tax evasion.

– Adriano and Dani Alves –

In May prosecutors accused Barcelona’s Brazilian defender Adriano of defrauding the Spanish state of 646,086 euros for ceding his image rights through an offshore company in Madeira, Portugal.

In June Spanish authorities disclosed that Barcelona’s former Brazilian international defender Dani Alves owed 1.3 million euros in overdue taxes and late payment fines last year.

– FIFA sanction –

FIFA in 2014 slapped Barcelona with a one-year transfer ban for breaking rules on signing international players under 18.

– Failed real estate operation –

A Spanish court on Tuesday ruled Barcelona must pay 47 million euros to a real estate firm over a cancelled land sale. 

Barca received 35.4 million euros in 2005 after agreeing to sell 10,000 square metres (25 acres) of land at L’Hospitalet de Llobregat in the south of the city to build 1,000 apartments and a hotel.

But strings attached to the sale meant the contract was not fully completed and the club was ordered to repay the cash plus interest and legal costs.