The four Middle English sermons from British Library, MS Harley 2268, for the occasions of the Annunciation/Passion Sunday, the Feast of St Mary Magdalene, a Procession, and a Dedication of an Altar to St Anne are edited here for the first time. They form an integrated group, sharing a consistency in content, a similarity of style, and a uniformity of outlook. Although clearly the work of a very scholarly preacher and replete with authorities both biblical and patristic, the tone adopted can also be a populist one, while the preacher makes use of images and allegories more often found in obviously literary works. Prepared at the peak of the Lollard threat and at the height of the turmoil of the Schism, the sermons provide an important example of outspoken and political preaching. Moreover, there is probably a wider range of implicit and explicit contextual information for the Harley 2268 texts than for any other similar set of sermons. This evidence gives strong support to the argument that the sermons were associated with the Benedictine Abbey of St Mary in York, specifically the abbot, Thomas Spofford, and were designed for different venues in York in the early decades of the fifteenth century.