The Book of the Dean of Lismore is a Scottish manuscript which was compiled in the first half of the sixteenth century. It contains a large collection of poetry including poems which indicate a connection with the north-west of Ireland. It is clear from the two poems by Giolla Críost Brúilingeach that he spent time in the court of Tomaltach Mac Diarmada in Lough Key in north Roscommon between c.1446 and 1458. It is also likely that he brought material back to Scotland on his return and that this may explain the presence of certain items in the manuscript. The Scottish poet was treated well by Mac Diarmada but there is no basis for accepting that he was slighted by the lord of Fermanagh, Tomás Mag Uidhir. On the contrary, he is unlikely ever to have visited Mag Uidhir and the poet’s satire was in all probability sponsored by Mac Diarmada for reasons which may be explained by local political circumstances. There is a connection between Giolla Críost’s poems and a poem in the manuscript by Fionnlagh Ruadh, Mac Griogóir’s poet. In this poem a comparison is made between Mac Griogóir’s residence in Scotland and that of Aodh Mac Diarmada in Ireland; the assumption has been that Aodh is Tomaltach’s brother and that Fionnlagh Ruadh must have visited North Connacht as did Giolla Críost. There is no certainty in this instance but, if Fionnlagh did visit Ireland, it seems possible that this was sometime between 1461 and 1465. Collectively, these Scottish poems are also a reminder of the broader context of literary transmission between Ireland and Gaelic Scotland in the late medieval period and of the importance of the backdrop of political and military connections.