In 1452, Matteo entered into partnership with the painter Giovanni di Pietro, and the two shared living quarters in the San Salvatore neighborhood of Siena in 1453.
That Matteo, at this time, is recorded as having colored and gilded a sculpture of the Archangel Gabriel by the celebrated Sienese sculptor Jacopo della Quercia is a reminder of the sort of tasks performed by an artist in the 15th century.
That Matteo had succeeded in establishing an artistic reputation is demonstrated by his selection as one of four Sienese painters who were to furnish altarpieces for the chapels of the Pienza Cathedral erected as part of the urban renewal of the town.
Dating to the years 1460–62, these paintings offer a secure point from which to evaluate Matteo's early style and to reconstruct his development as an artist.
Above this panel, in a lunette, is a Flagellation of Christ scene, which, with its violent action, twisted but anatomically correct bodies, and volumetric plasticity, shows a familiarity with the progressive Florentine draftsmanship of Pollaiuolo.