The 17th Century cup was given by T E Lawrence in 1933 to his godson, Ruthven Barrie Llewelyn Davies. Ruthven was the son of Peter Llewelyn Davies - one of five brothers adopted by J M Barrie - and widely regarded to have been the inspiration behind Barrie's most famous character, Peter Pan.
It is inscribed with the words 'RBLLD June 21st 1933 from his godfather T E Shaw'. It also reads "Lawrence of Arabia" and the words "For the imp: belated but will not know about time yet…TES".
The cup, which is estimated at £1000-1500, is part of a small collection originating from the Llewelyn Davies family appearing at the specialist silver and jewellery sale at Sworders' auction room in Stansted Mountfitchet.
It dates to the early 17th Century and was made in Germany by Paul Hubner.
The sale also features a Cartier lapel watch once owned by Gertie Millar. She was one of the most famous actresses and most photographed women of the Edwardian era.
Gertie, a working class girl from Bradford, became a successful showgirl and actress and married the Earl of Dudley in 1924. The Art Deco style lapel watch has the initials GM in diamonds and is believed to have been a gift from her husband. The watch has an estimate of £10,000-15,000.