Born in Buenos Aires, D'Alessandro spent six years in his country with San Lorenzo de Almagro, being part of the squads that won four Argentine Primera División championships.
In June 1974 the team played UD Salamanca in a friendly, and the Spaniards were so impressed they decided to purchase him, having to (successfully) deal with the Argentine Football Association first; players under 26 were prohibited from moving abroad, and he was 25.
[5] In late March 1994, D'Alessandro became Atlético Madrid's sixth manager of the season, being appointed as the side, led by elusive chairman Jesús Gil, was placed in the relegation zone;[6] the Colchoneros eventually finished in 12th position, and his contract was not renewed.
[10][11][12] In April 2010, after several years working as a sports commentator in both radio and television,[13] D'Alessandro returned to Salamanca for his third stint as a manager,[14] eventually avoiding relegation from the second division.
[16] His first match was a 5–0 home win over Catalonia neighbours CE Sabadell FC;[17] however, after not being able to prevent the final drop even though the results improved overall, he resigned.