The list, which contains more than 200 books, is very different from the literary canon which he produced in his previous job as chief executive of the Qualifications and Curriculum Authority.
Charles Dickens, Thomas Hardy, Emily Bront and Jane Austen do feature but so do many contemporary writers such as John le Carre, Nick Hornby and Martin Amis.
Winchester's dons (the school's name for its teachers) compiled the list at a meeting where they had to argue the case for their favourite titles.
"The discussion," as Dr Tate says in his letter to parents enclosing the selection, "was frequently heated. It was felt very strongly that all works included should have the merit of being well-written - though this proved to cause the liveliest discussion." Dr Tate then added some titles of his own.
There are eight sections with books aimed at boys aged between 13 and 18, fiction written in English; fiction in translation; science fiction; crime fiction; travel; war; works which don't fit another category and three works "produced by monomaniacs" (TH Huxley's The Courtship Habits of the Great Crested Grebe, TH Clarke's The Rhinoceros from Durer to Stubbs: 1515-1799, and Redcliffe N Salaman's The History and Social Influence of the Potato). Poetry is to have its own list.
The books are marked either A for younger readers or B for older ones, though some dons felt that no distinction should be made. Dr Tate's letter points out that the list is "entirely optional".
He said: "I wanted to raise the profile of reading in the school. People here do read obviously, but there are a lot of contrary pressures, even in a place like this."
And what would be his own choices? Anita Brookner's The Bay of Angels, Virginia Woolf's The Waves, Joseph Conrad's Nostromo and Guiseppe di Lampedusa's The Leopard.
THE A LIST
Anthony Burgess: A Clockwork Orange
Bram Stoker: Dracula
Margaret Atwood: Cat's Eye
Italo Calvino: The Non-existent Knight
Harry Harrison: Bill the Galactic Hero
Pamela Branch: Murder Every Monday
Robert Harris: Enigma
THE B LIST
Norman Mailer: The Executioner's Song
Samuel Johnson: The History of Rasselas
Carlo Levi: Christ Stopped at Eboli
Philip K Dick: Do Androids Dream of Electric Sheep?
Chester Himes: Cotton Comes to Harlem
Bruce Chatwin: In Patagonia
Ludovic Kennedy: Pursuit
Izaak Walton: The Compleat Angler
Tom Wolfe: The Electric Kool-aid Acid Test
Sir Thomas Browne: Pseudodoxia Epidemica
Dylan Thomas: Portrait of the Artist as a Young Dog
William Beckford: Vathek
A selection from the canon according to Winchester (and Dr Tate)