Robert [2nd son, eldest Hugh, ancestor of Willoughbys, feudal Lords of Cumberworth, Lincs]; allegedly married ? Orreby, daughter of one of the feudal Lords of Orby and Ingoldmells, Lincs, and died between 3 Feb 1256/7 and 21 Feb 1257/8. [Burke's Peerage]
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ROBERT DE WILLOUGHBY, 2nd but 1st surviving son, succeeded defacto to the family estates, presented to Willoughby in the Marsh church in 1227 and appears as tenant of Gilbert de Gant in 1242. He was appointed, 23 June 1246, to aid in the custody of the royal escheats in Lindsey, where he was escheator, March 1255/6 and at his death; was granted exemption from juries and recognitions, 1252 and 1255; and on 3 October 1255 he was given free warren in his demesne lands. He is said to have married a lady from the family of ORREBY, lords of Orby and Ingoldmells, Lincs (g). He died between 3 February 1256/7 and 21 February 1257/8. [Complete Peerage XII/2:656, (transcribed by Dave Utzinger)]
(g) In 1242 Robert shared lands in Fenton, Lincs, with Fulk de Orreby, he was in a lawsuit with Gilbert de orreby, Feb 1256/7, and his grandson Robert was a co-heir and an executor of John de Orreby in 1316. G. A. Moriarty suggests that Robert de Willoughby's unnamed wife was probably a daughter of John de Orreby of Orby, son and heir of Herbert, son of Alard, otherwise Herbert de Orreby, for whom see ante, vol. X, p. 168, note "c". This John was ancestor (great-great-grandfather it would seem) of John de Orreby to whom Robert de Willoughby, grandson of Robert abovenamed, was coheir in 1316.