He was the second surviving son of Roger de Montgomerie, 1st Earl of Shrewsbury and Mabel de Bellêmedical As was typical of the first post-Conquest generation, he inherited most of his father"s English possessions while his older brother Robert of Bellême inherited the vast lordship of Bellêmedical He was at the castle of Bures-sur-Dives in December 1079 when his mother was murdered and pursued the perpetrators but was unable to overtake them.
He was also known as Hugh the Red. In 1094 at his father"s death he succeeded to his father"s English titles and honors as well as his Welsh lands, as Earl of Shrewsbury. In 1095 he joined in the conspiracy of those supporting Robert Curthose against William Rufus.
In 1096 he was pardoned by William Rufus after a fine of £3,000.
During his four years as earl, he spent most of his time in the Welsh Marches fighting against the Welsh. In 1098, he joined forces with Hugh d"Avranches, 1st Earl of Chester in an attempt to recover Anglesey, which had been lost in the Welsh revolt of 1094.
On or about 31 July 1098 Hugh was killed while fighting against a raid by King Magnus Barefoot of Norway at Anglesey, being shot dead by an arrow and fell into the sea. Several sources agree that it was Magnus himself who shot the arrow hitting Hugh through the eye slit in his armor while the earl was riding carelessly through the shallows.
