In 1557, he raised one hundred men at his own expense and joined the Earl of Derby in his expedition against an invading Scottish army.
Apart from his military career he was also High Sheriff (six times between 1547 and 1588), Deputy Lieutenant of Cheshire (1569, 1585, 1587), Custos Rotulorum of Cheshire (1579 to his death) and High Sheriff of Flintshire for 1582–83.
[citation needed] Sir Hugh the younger (1552–1601) married Mary Holford and had five sons and three daughters.
[3] Their eldest son Robert was created Earl of Leinster in 1646; another son, Hugh, was the ancestor of the Marquesses of Cholmondeley; while yet another son, Thomas, was the ancestor of the Barons Delamere; his daughter Lettice Cholmondeley married Sir Richard Grosvenor, 1st Baronet.
His wife Lady Cholmondeley gained fame in her own right for her lawsuit against her uncle George Holford over the inheritance of her father's estates.