A few years ago, we showed that Robert Catesby, directly descended from Sir William Catesby, sought to kill James VI/I, a descendant of Henry VII, by gunpowder 120 years after Henry had Sir William hanged after Bosworth.
This second case, of which I was reminded in Kathryn Warner‘s The Despensers, doesn’t involve direct ancestry on both sides but does relate to a particular venue. Following the battle of Boroughbridge in 1322, Edward II had his Contrariant cousin, Thomas Earl of Lancaster, beheaded at Pontefract Castle. In 1400, Edward’s great-grandson Richard II died there by starvation, very probably at the behest of Henry IV, descended from Thomas’ brother.