The obverse depicts a seated female figure wearing a mural crown and in medieval costume (possibly representing the City of London), holding in her left hand an upright sword. Facing her is a standing soldier of the City Imperial Volunteers. The figures are flanked by two sets of three robed females facing inwards, blowing archaic trumpets from which hang banners bearing the Arms of the City of London. In the far distance, a troop of marching soldiers are visible. The reverse shows a hill surrounded by trees and surmounted by a flagstaff. Behind the hill the sun rises while in the foreground there are two field guns.

The City of London Imperial Volunteers were raised in December 1899 by the Lord Mayor of London and were equipped at the expense of the City Corporation. Recruited from men serving in the volunteer units in the London area, it eventually comprised two companies of mounted infantry, one battalion of infantry and one battery of artillery. The regiment embarked for South Africa in January 1900.