These two extraordinary figures in the history of Christianity were contemporaries, even if only for a few years between 1220 and 1226. But did they ever manage to meet in person? Yes they did. Their personal contacts, as far as we know, were minimal, and spread out over three brief meetings.
We know that Saint Anthony participated at the General Chapter of Mats, celebrated in Assisi in May 1221. Anthony, among the crowd, saw Francis and listened to his speech. In 1224, according to legend, Saint Francis miraculously appeared at the Chapter of Arles, while Anthony was holding a sermon for the monks on the theme of the cross.
The most important contact, however, is the third one. We have the testimony of a letter which Francis sent to Anthony, between 1223 and 1224, through which Francis authorizes Anthony to teach theology to the friars, but recommending him that this teaching did not come at the expense of prayer. The significance of this letter is in the investiture of Anthony as a preacher and teacher of theology.