Boi and Leonardo were invited to Lisbon by the nephew of Phillip II. He was Dom Sebastian I, King of Portugal. Both Italians played and beat Sebastian's champion, El Morro.
Both stayed in Portugal for some time. When Leonardo returned to Italy, Boi stayed on in Lisbon. He capitalized on his skill as a chess player, winning high stakes games. He was even able to give material odds or play blindfold or simultaneous games.
He went all over Europe playing in this way. He was making anything up to 8,000 scudi a day in winnings. It was during this period that his luck took a turn for the worst.