The Devon historian Tristram Risdon (died 1640) wrote of him: The hopeful Dennis Roll, esq., who though he were the youngest that ever had the government of this county committed unto him, to be commanded by a white staff yet managed he that place with such staidness as elder ages could not have performed better service to their sovereign nor done their country better credit, shewing himself so free hearted that he exceeded in liberality; but this bud soon blasted in the blossom.

[4]John Prince (1643–1723) called him The darling of his country in his time, adorn'd with all the desirable qualities that make a compleat gentleman.

Rolle loaned a large sum of money to Sir Bevil Grenville (1596–1643) in return for his written bond.

[8][9][unreliable source] On 1 September 1637 an agreement of mutual maintenance was signed by Rolle and his father-in-law and Elizabeth, Countess of Essex (died 1656), (Elizabeth Poulet, daughter of Sir William Poulet of Edington, Wiltshire, past High Sheriff of Wiltshire and cousin of William Paulet, 4th Marquess of Winchester), second wife of Robert Devereux, 3rd Earl of Essex (1591–1646), whom she had married in 1630 and separated from in 1631.

[19] His widow's wish as stated on the epitaph was not met and the couple's son Dennis died soon after his father, leaving only daughters who were excluded from the inheritance by entail.