It took 11 months before three years old, Maddie disappeared in Praia da Luz, when he was 29.
The pic has been revealed in the court documents about his arrest for the theft of diesel trucks in Portimao, in the Algarve.
Another snap, thought to be a passport photo, was taken in 1996, after his release from a German prison.
Brueckner, aged 43, was jailed for sexual assault on a six-year-old girl in a playground.
At the time of his arrest in 2006, he lived in a farm on the edge of the beach of Praia da Luz.
His Austrian pal Michael Tatschl reported to have said to the police Brueckner “was a very good burglar” who targeted rich tourists apartments.
He left Germany and turned up in Lagos, Portugal.
During this time, a lawyer friend of Gerry McCann accused the sacked detective Goncalo Amaral for “fantasy”, after saying Brueckner was a “scapegoat”.
The disappearance of Madeleine McCann
Amaral also made slurs against Maddie’s parents, Kate and Gerry, of Rothley, Leicestershire.
The lawyer, Rogerio Alves, said: “I don’t want to give any step of this guy.”