The history of Pistoia's Olivetani monastery dates to the second half of the 1300s when Bishop Giovanni Vivenzi blessed the first cornerstone placed on a piece of land with no other constructions around, in proximity of the city wall (vs8). The building was already completed a few years later and the complex, consisting of the church, the cloister and the rooms arranged around it, could host the general Chapter of the congregation which found a seat, for the first time, outside the walls of the mother church: the Abbey of Monteoliveto Maggiore near Siena. The great economic wealth achieved through the rich donations made to the monastery allowed the church to expand during the fifteenth and sixteenth centuries and to renovate the original complex. The more radical changes would be made around the middle of the seventeenth century when the church's hail was raised and vaulted. The four side altars were added at the same time. In the same century the façade was redone so that, of the original structures, only the choir with its ribbed Gothic vault remained unaltered. In the same period the cloister was frescoed, with the economic support of the major Pistoian families (vi).
In the 1700s further changes were made to the monastery but at the end of the century it was abolished by order of Bishop de' Ricci who made it the seat of the Ecclesiastical Academy as well as using it as his temporary home (vs20). The church's name was changed to San Leopoldo in honor of the Grand Duke who was a firm executor of de' Ricci's ideas and San Benedetto served as the seat of the Diocesan Synod that ratified the Pistoian bishop's reforms. After that time, the church and monastery fell into a period of abandonment due to the improper uses that it served; during the French occupation, for instance, it was used as a barracks. In the first half of the next century the complex was joined to the episcopal seminary by a corridor as long as the Street that is today known as via del Seminario. The church houses a fresco of the Annunciation by the Pistoian painter Giovanni Cristiani (vs40/41/48)as well as a panel portraying Saint Francesca Romana by Giacinto Gimignani (vs46/47).
The monastery, after restoration, todayhouses a center for the elderly while the church serves parochial functions.

(n.) refers to the number of the file-card (s.i.) means see information inside

Just after the mid seventeenth century, the abbot Ippolito Bracciolini summoned Giovan Battista Vanni, already in his sixties, to decorate the cloister with frescos. it is the last work by the Florentine painter who died after completing the cycle in Pistoia. The work is composed of twelve lunettes that illustrate, in a lively and narrative tone, Stories of the Knights of the Order of Saint Benedict.