As one of the best students, he was sent to the Studio generale in Rimini to complete his studies, and then entered the seminary there in 1423.

[1] After he was ordained as a priest, Oliva became a professor at the Augustinian convent at Perugia, a post he held for twenty years.

[1] In 1439, he was elected to a three-year term as provincial superior of his order for the March of Ancona.

[1] During this period, Oliva delivered many sermons throughout Italy, especially in Naples, Siena, Florence, Bologna, Mantua, Ferrara, and Venice.

In 1460, he traveled to Ancona to receive Thomas Paleologus, the deposed Byzantine Emperor.

[1] On 16 November 1461 he was named apostolic administrator of the see of Camerino, a post he held until his death.