One of the school's earliest sites, dating from the 15th century, can still be seen adjacent to St Oswald's Parish Church.

Oswestry School was founded in 1407 by David Holbache, Member of Parliament for Shropshire and Shrewsbury, and his wife Guinevere.

Later in the 15th century it took up residence in the ancient half-timbered building close to the Parish Church of St Oswald.

Early archive records show that a small percentage of the subsidised school-fees was set aside to pay for cockfighting, the pupil entertainment of that time.

Its closest neighbour, the neo-Gothic Victorian chapel, built in 1863, stands looking across at St Oswald's Maes-y-llan battlefield, now the school's extensive playing fields.

[9] Senior boarders and day pupils now mingle in the 'competitive' houses: Burnaby, Donne, Oswald and Spooner.

[10] Here are just some of the current and historical houses: In the 19th century, an Old Oswestrian wrote the school's Latin song, 'Hymnus Oswestriensium', which is informally known by its first words, 'Gaude Plebs'.

Moreton Hall was founded in 1913 by the widow and daughters of Oswestry's late headmaster, John Jordan Lloyd-Williams.