The first Mayor of Oswestry was Richard Pope, who was named as such in the Oswestry charter granted 13 January 1674. Thereafter, in accordance with the charter, the Mayor was elected annually on the Friday after Michaelmas (29 September). Under the Municipal Corporations Act 1835 the date of election was changed to 9 November from 1836. Under the Representation of the People Act 1948 the date of election was again changed, and since 1949 the annual election has been held in May. Emily Gertrude Rogers, who was elected Mayor in November 1947, continued in office until the election under the new system in May 1949.

Some biographical details are given in The Records of the Corporation of Oswestry edited by Mr Stanley Leighton, with an Account of the Mayors, Stewards, Recorders and Town Clerks by Mr. Askew Roberts (reprinted from Transactions of the Shropshire Archaeological Society, 1879-1883).