The fourteenth century brought a number of challenges to the house at Oxford. From 1370 to 1382 there was the presence of John Wyclif (a priest, but not an Augustinian).

Although the Augustinians had been attracted initially by his thoughts about the abuse of wealth by the Church and about social problems that the church was reluctant to challenge, none followed his theology (much of it based on his interpretations of Augustine) that led to his condemnation by Rome in 1382. The Augustinians at Oxford had good reason to sympathise with Wyclif’s opinions in the early stages of the controversy he generated.

Since disputations were regularly held in the Augustinian convento, it is not especially important that Wyclif was lecturing there when he received the news of his condemnation. But many of his beliefs were derived from the greatest of Augustinian theologians, Giles of Rome, and the later Prior Provincial of the English Augustinians, Thomas Winterton, was one of Wyclif's close associates. After the authoritative condemnation of Wyclif’s opinions, there was, however, no reason to question the orthodoxy of the Augustinian friars at Oxford or within the Austin Friars generally. For example, an Austin Friar, John Schypton, was among the twelve doctors who approved the decree condemning Wyclif's doctrines on the Eucharist. The decree was promulgated in the school of the Austin Friars in 1381, where Wyclif himself was lecturing. Thomas Winterton (or Wyntirton), another Austin Friar, and contemporary of Wyclif at Oxford, published a treatise entitled Absolutio against Wyclif's Confessio. 

Wyclif counted Winterton among his boyhood friends, but Friar Thomas entered the fray without fear or favour. He took the Confessio of his former friend and picked out ten different heresies and refuted them from the Church Fathers. The historian, John Leland, who wrote during the era of Henry VIII, spoke highly of the Winterton’s ability as a theologian and a writer, while H. B. Workman paid tribute to the Christian manner in which the friar carried on his controversy -  a virtue not always practised in medieval theological discussions.

Among the other Oxford-educated Augustinians who took part in the proceedings against Wiclif and his followers were Thomas of Ashborne, John Banekyne (or Bankyn, who who composed his polemic Contra Positiones Wiclevi - "Against the Positions of Wyclif"), John Courte, Robert Waldeby, afterwards archbishop of Dublin and finally of York, and John Waldeby about this time English Provincial of the Austin Friars. Peter Pateshull, who became a Lollard and made violent attacks on his Order, was an Austin Friar and had obtained his magisterium (Doctor of Theology degree) at Oxford.

The second challenge was the positive effect of the Great Western Schism (1378 to 1418) upon the number of Augustinians studying at Oxford. As Wyclif came to his mortal end, the papacy at Avignon had just ended, and the Great Western Schism had just begun. During this schism, the Augustinian houses at Oxford and Cambridge were used to capacity. One reason for this was that the General Chapter in Wurzburg in 1391 forbade Augustinians to study in Paris as long as it supported the Avignon Obedience (as opposed to the Roman Obedience). But Oxford and Cambridge had a rule that one religious of an Order could be promoted each two years, and the influx of foreign students stopped when the schism ended, the more so because new universities were established on the Continent, and those of Bologna and Padua now surpassed the English universities in quality. 

In the fifteenth century John Barnard, theological writer and Austin Friar, is said to have been chancellor of the university in 1412. It is probable that John Lowe, provincial prior of the English Augustinian Province in 1428, afterwards bishop of St Asaph and of Rochester, principal founder of the great library of the Austin Friars of London, and the famous John Capgrave, Augustinian Provincial in 1456, studied at Oxford. Thomas Penketh O.S.A., Provincial of the Austin Friars in 1469 and famous for his knowledge of Duns Scotus, taught theology there in 1473 and 1477. William Galyon (1507) provincial prior and reformer of his order, was a student in this convent.

By the year 1427 the attendance at Oxford and Cambridge declined, and English members of the Order were able to take the unused places that previously had been occupied by foreign Augustinians. One English Augustinian who received benefit from this fact was William Galyon O.S.A. of Lynn, who at his death around the year 1507 was almost the last of the Augustinian scholastic tradition of Oxford doctors of divinity. Ten years later, the gross enrolment at the University of Oxford had fallen below 1,000. When he was Provincial of the Austin Friars, John Capgrave (mentioned above) in 1455 attempted to give a necessary financial boost to the Augustinian studium generale there, which was his own alma mater.

He helped the impoverished house by granting the privileges of founder to Sir Edmund Rede of Boarstall, a descendant of Sir Haudlow of Boarstall. Haudlow was really the founder or at least the chief benefactor of Oxford. He was a knight in Kent and having killed a man in self-defense in 1269, he apparently atoned for his deed by endowing the Augustinians' Oxford friary, in which the king took a great interest. Indeed, his gift may have been the fine imposed by the king on Edmund Rede for the act of murder. The recognition of Rede with the title of founder gave him stature and burial rights in the Austin Friars' chapel, and gave the Austin Friars of Oxford some additional regular income.

William Becchi O.S.A. of Florence was elected Prior General at the General Chapter at Siena in 1460, and in his administration proved to be quite forthright and somewhat severe. In March 1461 he deposed the Priors of the Austin Friaries at London and Oxford “because of their poor administration,” and then placed these communities under the supervision of three vicars of his choice, one of whom was an Augustinian who is remembered in the history of early English literature, Osbern Bokenham O.S.A. It was in 1461 the Augustinian house also had its status as a studium generale (i.e., being an international study house of the Order) withdrawn by the Prior General, which was a somewhat belated attestation that its earlier prestige had by then dissipated.

On 8th March 1473-74 King Edward IV was willing to help alleviate the poor financial condition of the friary. This is evident from a royal charter that is still preserved in the monument room of Wadham College (i.e., on the former site of the Austin Friars in Oxford). It relates that in 1474 King Edward IV granted the Augustinians at Oxford the right to hold an annual fair in front of the gates of friary from 5th May to 10th May. The proceeds were to go towards their maintenance. The “Austen frayrs fayre" attracted merchants and buyers from as far as London, which was fifty kilometres away. It is interesting to note that during the week of the fair the Augustinian procurator (bursar) of the friary was delegated to hold a court of justice, with powers to arrest and imprison for the purpose of redressing any disorder within the fair grounds. The fair was in 1538 said to be worth £4 or £5 to the Augustinians, and seems to have been of considerable importance to the neighbourhood.

In 1488 a considerable bequest of one hundred marks to the house was insufficient to "save its crumbling walls." In March 1489 three Oxford Agustinians found themselvers in jail. For protecting Thomas the Sealer, a servant of the abbot of Abingdon who was accused of theft, the Austin Friars Thomas Thwates, Prior of Oxford, John Cope, subprior, and Stephen Courtys, a bachelor in theology, were jailed. By letter, King Henry VII ordered the alleged thief to be delivered to his representative, Robert Chamber, before whom the Austins are also to be examined. After a few days in jail the friars were pardoned upon the intercession of the University. By 1516 the English Province obtained a prospective means of income that in hindsight indicates some desperation and a very poor - a desperate? - reading by Rome and by the local Augustinians of the contemporary ecclesiastical mood in England.

Arrangements were made to sell plenary indulgences, which method had been used in regard to the Austin Friars at Cambridge in 1494, but the ecclesiastical and theological climate in England had changed considerably between 1494 and 1516. The selling of indulgences in England in 1516 - on the very cusp of the outbreak of the Protestant Reformation in Germany - had the opposite effect to that intended by causing financial difficulties throughout all of the English Augustinian Province. The sale was to continue for ten years; remarkably, some documents that detail the contract still exist, and one such document includes the following paragraphs:

"The Holy See grants to Austin Friars in Oxford and to the other English houses of the Order a plenary indulgence for ten years on the Wednesdays of the four Ember weeks, from Ash Wednesday to the First Sunday in Lent inclusive and from Palm Sunday to Easter Sunday inclusive. Silvio Passarino, papal datary and chamberlain, to receive half of the proceeds with the exception of 200 gold ducats which are to go yearly to the papal treasurer for expenses. The boxes containing the contributions must be provided with three keys, one to be held by the local prior, one by the superior of the Observant Franciscans and one by Ralph Maruffus, merchant of Genoa and papal representative in this matter.

(Continued on the next page.)

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