Watch List notes:

Education / Politics, William Pitt, the younger and Merchant Taylors' School, glazed silver prize medal, awarded to William Herbert Maddock, 24 June, 1858, the Pitt Club Exhibitioner, by B Wyon, bust of Pitt right, rev details engraved within wreath, 46mm., silver frame with suspension loop and ring, nearly extremely fine and very rare
The medal's recipient would seem to be the William Herbert Maddock (b. 1841) who, in the 1881 census, was listed as "Schoolmaster, MA Oxon, Clerk in Holy Orders" at Kington, Herefordshire.

Estimate: 80 - 120 GBP