The first dated work by Benvenuto to come down to us is an Annunciation and Saints (1466) in the church of San Girolamo in Volterra, for which the artist also painted a Nativity (1470) and a predella with stories of the life of Christ, now in the Volterra Pinacoteca. Also of 1470 is the Annunciation panel in the church of San Bernardino in Sinalunga. During this period Benvenuto's artistic idiom, which in his earliest phases clearly shows the influence of Vecchietta and the naturalistic vision of Domenico di Bartolo, acquires its individualism. This is due in part to his prolonged contact with two North Italian miniaturists who were active in Siena, Liberale da Verona and Girolamo da Cremona. Under their influence Benvenuto's noble, classical forms congeal to a hard, intensely lit, brightly colored, and glassy consistency, inserted into solidly balanced compositional structures. Masterpieces from this sharply defined, immaculately surreal world are the triptych from Montepertuso (dated 1475, now in the parish church of Vescovado di Murlo, near Siena), the Borghesi altarpiece in the church of San Domenico in Siena (1475-1477/1478), and the triptych in the National Gallery, London (1479).

In the 1480s Benvenuto was commissioned to prepare designs for the floor decoration of the Siena cathedral and miniatures for its choir books (now in the Libreria Piccolomini) and for those of the monastery of Sant'Eugenio near Siena (now in the library of the abbey of Cava dei Tirreni). For Sant'Eugenio he also realized the large Ascension of Christ altarpiece, signed and dated 1491 (now in the Pinacoteca Nazionale in Siena; the predella panels are at the NGA), a work in which his severely classical language, charged with a latent expressive passion derived from northern painting, achieved its most intense results. In the following years his works show a simpler, more schematic compositional structure and more pleasant, sometimes sugary expressions, in part because of increasingly frequent collaboration with his son, Girolamo di Benvenuto. Nonetheless, despite the identical composition of two large panels of the Assumption of the Virgin pictures, both of 1498 (one formerly no. 10.148 in the Metropolitan Museum of Art, New York, signed by Benvenuto, and the other in the Museo d Arte Sacra in Montalcino, signed by his son) the styles of the two artists are clearly distinguishable. At the beginning of the sixteenth century the older master's works reveal incrementally the exhaustion of his creative imagination and a recourse to tried and true formulas from the past, as in the case of his last signed work, the Madonna and Child with Saints in the church of Santa Lucia in Sinalunga, dated 1509. [This is the artist's biography published, or to be published, in the NGA Systematic Catalogue]