 Born in Mendoza, Astudillo started his career in the Argentine second level with Godoy Cruz Antonio Tomba of Mendoza Province.In 1997, he was signed by Gimnasia y Esgrima de Jujuy of the Primera División, and two years later moved to Deportivo Alavés in Spain.An instant first-choice, Astudillo scored four league goals in his first season, and was instrumental in the Basque side's runner-up run in the UEFA Cup the next year.