A vast amount has been written about Anne Boleyn (1501/07-1536) and her relationship with Henry VIII (1491-1547), particularly concerning her role in Henry’s quest for a male heir and whether she is to be regarded as ‘harlot or heroine’. Yet some key questions surrounding Anne’s life and her relationships with Henry VIII and Elizabeth I are still not completely resolved.Amongst the most significant are: her age and precise date of birth; whether she was ‘guilty as charged’ of adultery or not; andher legacy and impact on her daughter, Queen Elizabeth I. This paper takes a new approach to these issues by investigating not only written historical sources but the role of particular objects that can be used to add to the continuing debate. Examination of actual artefacts is important in historical research as well as written material. The items considered hereare:an undated Letter on which the dating of Anne’s birth rests; the Handkerchief that Anne gave her alleged lover in May 1536 suggesting a link to Shakespeare’s Othello; and a Tablecloth featuring Anne’s symbol of a falcon made in 1571. The paper discusses the likely validity of three distinct but overlapping argumentsrelated to these objects, demonstrating that these questions are worthy of continued further investigation. It also, and more significantly in terms of historiography and the history of objects in the early modern period, demonstrates the value of material evidence.