Diego Cavalieri was a member of the Brazilian team that won a second title at the 1999 edition of the FIFA Under-17 World Cup in New Zealand. Diego Cavalieri and his Brazilian teammates were drawn in a tricky group ahead of the tournament. They were in Group C alongside Germany, Australia and Mali.

Rubinho and Diego Cavalieri were the only goalkeepers in the Brazil squad according to the goalkeeping requirement for each participating team at the tournament. Rubinho was the starting goalkeeper, while Diego Cavalieri had to settle for a place on the bench throughout the tournament.

Brazil began their Group C campaign on a winning note thanks to the goals from Marquinhos and Carlos Henrique either side of the interval. Marquinhos gave the Brazilians the lead just after the half hour mark before Carlos Henrique doubled the advantage midway into the second half. Australia pulled one back through Dylan MacAllister with nine minutes left to play to setup a grandstand finish, but Brazil held on to take the win via a 2-1 scoreline. In their second group outing, Brazil and African team Mali played out a goalless draw and the same scoreline was recorded against the Germans in their last group outing. The two draws from the last two games ensured that Brazil finished second in Group C behind leaders Australia who had six points as the two teams progressed into the last eight.

Brazil sealed a place in the semi-finals thanks to the 4-1 win over fellow South American team Paraguay. Leonardo was the star of the show with three goals, while Caca scored the other Brazilian goal. Paraguay scored their lone goal through Alejandro da Silva.

The Brazilians sealed a final meeting with Australia via a 4-2 win over Ghana on penalties. The two teams had shared four goals in regulation time and then extra time. For the final, Brazil had beaten Australia in the group stage and they repeated it again to win their second World Cup title at the Under-17 level. Brazil beat Australia 8-7 during penalty shootout after the two teams played goalless at the end of 120 minutes.