He was the elder son of a fairly prosperous Lincolnshire landowner who served on a few royal commissions during the early 1360s, but otherwise lived quietly at his home in Somerby. Robert is first mentioned in 1371, when he witnessed a local deed. Three years later he and his mother, Katherine, presented jointly to the chapel of Stain. 
Robert, son and heir of Thomas Cumberworth by his wife Katherine, married Sibyl, daughter and coheir of Sir William Ergum. 
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