It was owned by Bruce of Cowden and used by Bonnie Prince Charlie during a meal to drum up support for the Jacobite uprising in 1745.
The glass, engraved with ‘God Blis King James the Eight’, is valued between £8,000 and £12,000.
It was common place to break the foot of a glass used by the Prince so that no lesser toast could be given.
The engraved foot of the glass shows that the Prince toasted his father King James - and in this case, no lesser man could drink from it.
It will be sold at auctioneers Lyon and Turnbull’s Scottish sale on August 16.
As it was such an important glass it was repaired for the Bruce family by goldsmith Patrick Murray from nearby Stirling.
John Mackie, a specialist at Lyon & Turnbull, said that any items from the Jacobite era tended to go for a good price at auction.
He said: “There is a huge interest in Jacobite items and they always seem to do well at auction. It is an interesting part of history.”