The bond between two Lieder composed by Oswald von Wolkenstein, Kl. 109a and 109b, has been the subject of several studies, which have led the Oswald scholarship to interpret the second poem as a more or less literal (auto)translation in German of the first one, written in Latin. However, significant discordances may be observed in both length (two stanzas in Kl. 109b, nine in 109a) and contents: the Latin text is a Glossenlied whose primary purpose is to praise the Virgin Mary, while Oswald’s supplication towards her seems to play a pivotal role in Kl. 109b. This study sheds light on this pair of poems and offers a new key to understanding not only their bond, but also their role within Oswald’s corpus.