Gianfrancesco Penni
Born in Florence to a family of weavers, Penni entered Raphael's workshop very early in his life, and collaborated with him on several works, including the famous Rooms of the Vatican Palace, as well as the frescoes of Villa Farnesina, both in Rome. Heinrich Wölfflin and some other writers credited him with the entire execution of the Raphael Cartoons, with Raphael only creating the initial design, though more recent writers believe Raphael did much of the work himself.
Aldobrandini Madonna
Aldobrandini Madonna, one of several small and mid-size Madonnas painted by Raphael in Rome, was likely something he worked on in his spare time of projects for the Pope or members of his court. During this time period, Raphael was painting the Stanza della Segnatura, the first room in the Vatican Palace to receive Raphael and his workshop's frescoes.