Through his Grey relations he had connections with the House of York, as his uncle Thomas Grey was executed as a result of the Southampton Plot in 1415, and his cousin, another Thomas Grey, married the earl of Cambridge's daughter; Cambridge had also suffered the same fate for his involvement in the plot against King Henry V. His family came from Northumberland, where his father had been constable of Norham Castle, Sheriff of the honour, and its MP. He had died in 1436, at which point Robert Ogle entered into his inheritance.
Royal Service
Ogle's career as a servant of the crown began prior to his father's death. In 1434, he was a commissioner of the Truce with Scotland, and a year later appears to have been captain of Berwick Castle, which was worth circa £194 in peace time, with another £200 to be paid in time of war. It was in which post he was captured by the Scots, during a border raid, and ransomed for 750 marks. As the king traditionally paid the ransoms of those captured on his service, Ogle applied for such; but the condition of the Lancastrian crown's finances at the time were such that he was still trying to get this compensation seven years later. He was later appointed Sheriff of Northumberland.
Elevation to the peerage and service to the new regime
He was created Baron Ogle on 26 July 1461, having been "the principal Northumbrian gentleman to support the Yorkist cause." He was further placed in command of the Earl of Northumberland'sforfeited castles- Alnwick, Warkworth, and Prudhoe. He also received in 1438 the earl's position of Warden of the Eastern March. He continued his diplomatic work on the border, completing, in October 1461, a further year's truce with Scotland. In 1465, with the elevation of Warwick's brother Montague to the earldom of Northumberland, the Percy estates that Ogle had received were transferred to Montague; Ogle was compensated with the Lordship of Redesdale and Harbottle Castle and other forfeited lands in Northumberland. He was a regular, if partisan, member of the King's Bench commissions in Northumberland, being regularly appointed by the Nevilles, first Salisbury, then Warwick. Ogle died on 1 November 1469. At some point, he had married one Isabel Kirkby of Kirkby, Lancashire, producing a daughter and three sons.He was succeeded by his eldest son, Owen Ogle, 2nd Baron Ogle.