The two saints were contemporaries for six years, from 1220 to 1226, in the order of the Minor Monks. Their personal contacts, as far as we know, were minimal, spread out over three brief meetings.

1. We know that Saint Anthony participated at the General Chapter of the Mats, celebrated in Assisi in May 1221. It lasted about one week and a varied assembly of 3,000 monks participated in it. Anthony, among the crowd, saw Francis and heard him speak. That is it. We have no evidence of a meeting between the two saints. Given the situation, it would have been impossible. Francis was overburdened with problems, thick and urgent, and he was not in good health. His time was carefully scheduled. Those attending were disorderly. Anthony was only a young novice, unknown by anyone, back from a failed missionary expedition: he was a personality that had yet to emerge.
2. The only testimony we have of a second contact between the two is an affectionate note, full of veneration and esteem, that Francis sent to Anthony "his bishop," between the end of 1223 and the beginning of 1224 in Bologna. With this, he authorised him to teach theology to the monks, but asking him to ensure that this did not interfere with prayer. The significance of that note is that Francis invested Anthony with the role of preacher and teacher of theology ex cathedra. It is the historic seal on Anthony's decision and the way in which Anthony embarked on the road of predication. The note also represents the direction which the Franciscan movement would take: to come into line with the pastoral needs required by the historical and the ecclesiastical moment, as their Dominican contemporaries had decided. Another sign of this direction was a change in the style of predication: the modus concionandi, typical of Francis, was completely set aside to return to the development of a traditional religious sermon, which the saint enriched and elaborated upon.
3. A third "meeting" has Francis as its main actor. He appeared at the Chapter of Arles, in 1224 (the days of the stigmata!), while Anthony was holding a sermon for the monks on the theme of the cross. Only one monk, Monaldo, had a vision, not even Anthony did; the others participated in its presence only indirectly. However, this was still in the context of an assembly, not an intimate, friendly meeting held apart in confidence. The image of the praedicator is the one that most commonly identifies Anthony's presence in the Franciscan Sources. It is interesting to note the reference to an assembly - during a Chapter - of monks convened to be prepared for predication by scholarly men like Anthony.