Robert may have been the eldest of Adam's sons. His name appears on several court records in Shenandoah County, Virginia.
On May 1774, Robert Cunningham was arrested for debt to Alexander Macher. On the same day, Robert was arrested along with Lawrence Bookin for debt to James Allen, assignee of Taverner Beale. Adam Cunningham posted bail.
In 1775 Robert was listed on John Netherton's census list in Dunmore County with 1 white male over 16 years, 3 white males under 16 years, and 5 white females.
An inventory for the estate of Robert Cunningham, deceased was filed in Shenandoah County in 1781. His estate settlement was filed 26 Oct 1784.
Johnathan Clark recorded in 1786 that "Rachel Cunningham, widow of Robert Cunningham, deceased, was living on land that was part of the claim of Walter Cunningham deceased." Five acres were cultivated and in bad order. The property contained two very old bad cabins.
Rachel was exempted from Shenandoah County taxes in 1787.
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