Most likely to have been born in Holborn, London, between 1548 and 1552, Fleming matriculated at Peterhouse, Cambridge as a sizar (a poor student performing duties in return for his tuition) in November 1570, and graduated with a B.A.
[1] It is likely that Fleming interspersed his studies at Cambridge with extended visits in London to write and translate popular texts on a range of themes, some of which remain in print today.
He began his career in spectacular style, becoming the first person to translate a complete Virgilian text (the "Bucoliks" or Eclogues) into English in 1575.
Later in his career Fleming was called upon by other authors to write recommendations for their books and worked alongside notable authors such as George Whetston, Barnabe Googe and Reginald Scot; many of Elizabethan London's leading printers called on Fleming to edit or embellish pre-production texts and he established a network of contacts.
Fleming died at Bottesford, Leicestershire, on 18 September 1607, while on a visit to his brother Samuel, the rector of that parish, and was buried under the chancel inside the church.