Lying almost in the centre of England, Leicestershire has assumed a strategic importance from at least Roman times. The Fosse Way, which connected the Roman camps at York and Lincoln with the recreational hot springs at Bath, bisects the county and passes through the then sizeable Roman settlement of what is now called Leicester. Watling Street, too, which provided contact between London and Chester, marks the south-western border of the present-day county.

The ninth-century Danes, like the Romans before them, also recognized the area's military significance. Leicester, along with Derby, Nottingham, Lincoln and Stamford, was one of the famous Five Boroughs, control of which was seen as so important to the consolidation of the Danelaw and its possible extension over what remained of Anglo-Saxon England. Danish insight did not escape the notice of Edward the Elder who realized that his success in reasserting Anglo-Saxon dominion over the Danelaw depended upon the capture of these towns. The line of fortresses built by king Edward and his sister, Æthelflæd, lady of the Mercians, suggests that both sides understood that the midland area held the key to the domination of England. Æthelflæd, in particular, used her fortified boroughs at Tamworth, Stafford and Warwick as bases to threaten, and eventually capture, Danishheld Derby and Leicester.

In the post-Conquest period, Leicestershire's importance was no less marked.