The 40-year-old Brazilian was partnered with one of the prison workers for the encounters which they lost after his magic touches failed to come to his rescue.
According to SunSport, the former AC Milan star and his teammate were beaten by a team of ex-force-men, who were disgraced out of service.
This defeat was, however, the first Ronaldinho would encounter since he became an inmate of the Paraguayan prison in Asuncion.
Reports claim that the former midfield star scored five and assisted six others in one of the games earlier this month.
His skills and pace could not save him from the double defeat his time as the opponents got the better of the former World Cup winner.
He was said to have borrowed the trainers of a warder after being urged to join the novelty game where he had the chance to show off his superb skills in a white vest top and black and white swim shorts.
Meanwhile, the former world player of the year was said to have been spending more time in a carpentry workshop.
It is unsure if the legend was learning new skills but he celebrated his 40th birthday on March 21 with a low-key barbecue.
Our correspondent earlier reported that former Barcelona star Ronaldinho has now turned his attention to another thing inside Paraguay prison by learning carpentry work and also teaching inmates football skills.
Presently, the World Cup winner does not know when he will be released from prison after being accused of using a fake passport to enter Paraguay with his brother.
As it is now, Ronaldinho could be sent to six months in jail if authorities in charge later come out that he is guilty of what he has been accused of.