Five Roberts

First Robert Ogle, before 1295-1350, 7th generation:
In 1305 Sir Robert Ogle was gifted land in Ogle from his father John. It is thought that the land was a wedding gift, because he married Margaret Gubium and the witnesses to the transaction were Hugh and Roger Gubium. The date suggests that Robert was of age or at least nearing adulthood. The land was called Northstrother and was located in Ogle. Hugh Gubium was the Sheriff of Northumberland around 1284.
Sir Robert Ogle was the first in a succession of five Roberts leading up to Robert, First Lord Ogle. This Robert had an illustrious Military career, mostly defending England from Scottish invaders. In 1319, King Edward II officially thanked Robert for his services.
In 1345, Robert killed Scottish commander Sir Alexander Staghan. In 1346 the Scots, under the command of David II invaded Durham. Lords Neville and Percy, Sir Robert Ogle, and Sir Robert Bertram defeated them at Neville's Cross. David II was taken prisoner and held for a time in Ogle castle.
Robert died in 1350. He and Margaret Gubium Ogle had two children, Sir Robert Ogle, 1306-1362, and Sir Alexander Ogle, died 1355.
Second Robert Ogle, 1306-1362, 8th generation:
In 1346, Robert and his father were both at the battle of Neville's Cross, where 12,000 Scots led by David Bruce II were defeated by 7,000 English soldiers led by Ralph Neville. Scots William Douglas and Malcolm Fleming were captured,and commanded to be held in the Tower of London. After either releasing or losing custody of Fleming, Sir Robert Ogle and twenty-nine other knights were arrested and taken into custody, and their properties seized, by the king's orders. By the following year, all of Robert's properties were restored to him and he was rewarded for the capture of William Douglas. Robert's brother, Sir Alexander Ogle, was killed when Berwick was captured in 1355.
Around 1331 Robert married Joan Hepple and received gifts of land from his father in law, Sir Robert Hepple. Children of Robert and Joan were Sir Robert Ogle, 1351-1395, Joan Ogle of Swinburne, married to William Swinburne of Capheaton, Thomas Ogle, 1352-1366. Joan and William Swinburne's son William Swinburne became a major land owner in Northumberland and represented the area with an appointment to the House of Commons in Parliament in 1395.
Third Robert Ogle, died 1355, 9th generation:
Sir Robert Ogle, knight married Elena Bertram who was the sole heiress to the Bothal estate and Bothal castle. Bothal was a barony and for many generations thereafter, their descendant heirs were known as "baron of Ogle and Bothal". Robert died before his father, leaving his minor son with his wife and his grandfather, Sir Robert Ogle, who died in 1362.
After Robert's death, Elena married twice more, first to John Hatfield, then to David Holgrave. Robert was the only child of Robert and Elena. in 1377, Blanche, the widow of Elena's father, Sir Robert Bertram, granted a lease to the castle of Bothal to Elena and her husband David Holgrave. David Holgrave died shortly before Elena, and her son was bequeathed the barony of Ogle and Bothal. The Ogle chapel in Hexham Abbey, lost in the 19th century, had a stone burial slab with the names of Robert Ogle and Elena Ogle.(1)
Fourth Robert Ogle, 1351-1409, 10th generation:
The son of Robert and Elena, Robert was born the eighth of December, 1351. By 1372, Robert had already married Joan Heton. His father had died when he was three years old. Robert had inherited the baronies of Ogle, Bothal, and Hepple. Robert was raised by his grandparents,Robert and Joan, until his grandfather's death in 1362. While a minor, Robert was the ward of John Phillipot and his wife, Joan.(2)
On 10 July, 1386, Robert was appointed conservator of a truce with Scotland. In 1388, Sir Robert Ogle, Sir Henry Percy, and many others attacked Scottish forces in Otterburn, but were taken captive. Sir Robert Ogle was knighted during the reign of Richard II. In 1391, Robert was witness to a quit-claim deed to David Holgrave and his wife Elena, Robert's mother. Elena died the year after her husband's death in 1405. In 1406, Robert became indebted for 10,000 marks to his son John, who had taken the surname Bertram after his grandmother. Robert promised John possession of Bothal castle as part of the deal, while willing to his other son Robert the family possessions of Ogle, Shilvington, Saltwick, Twysell, Seaton, Woodhorne, Sharperton, Shipbanks, Newhall, Hepple, and Lorbottle.
Robert died on 31 October, 1409 and was buried in Hexham Abbey under a black marble slab. Robert and Joan had four children, Sir Robert Ogle, 1380, Joan Ogle, 1374, Sir John Bertram, baron of Bothal, married to Joan Loudham. John took the surname Bertram in deference to his grandmother, returning Bothal to the Bertram name. John's son, William Bertram, appears to have been the baron of Bothal after John's death in 1449. John was a knight and had many occasions to fight alongside his Ogle kin. Joan may have died very young. Marjery married Robert Raymes.
Fifth Sir Robert Ogle, 1380-1436, 11th generation:
The earliest record of Sir Robert Ogle was in 1400 when he was taken prisoner by the Scots and 100 marks was paid as ransom to effect his release.(3) In 1401 he was summoned to attend the king's council at Westminster. By 1403, he had been appointed constable, justice, seneschal, excheator, and sheriff in Northamshire and Islandshire.
Although Robert had inherited much of his father's Ogle estate and other land holdings, he was jealous of his brother, John Bertram's inheritance of Bothal castle. On 1 November, 1409, the day after his father's death, Robert brought two hundred men to seize Bothal casle and after four days of heavy battle, he evicted his brother.(4)  On 13 February, 1410, John Bertram petitioned the House of Commons to request that the king restore his rightful property, which was granted. The sheriff of Bothal removed Robert and his soldiers and issued a proclamation that Robert should appear before the king to answer to the charges, and be imprisoned until payment of fines and financial amends made with John for damages to the property. By May, Robert had satisfied all of the judgements and his own lands and properties had been officially restored.(2)
After participating in more skirmishes between the Scots and English, in 1411, Robert was fighting alongside John, son of king Henry IV and Sheriff of England, at Berwick castle against the Scots. In 1413, he and Robert Umfreville were empowered to negotiate a truce by sea.(6) By 1415, Robert was known to own six castles and towers, and after his mother's death he inherited the Heton family's Ellingham estates. Also in 1415, king Henry V commissioned Sir Robert Ogle and Richard, Lord Grey to negotiate a truce with the Duke of Albany. He became a representative to Parliament in 1415. In 1416 he was high Sheriff.
In 1419, William Halliburton and his army took the castle of Wark and executed the guards. Sir Robert Ogle led a troop of soldiers into the castle through a drain which terminate at the river Tweed, and regained control, executing the Scottish invaders. The Scots complained that the English troops had invaded during negotiations of a truce and had slaughtered Scottish officials.
In 1399, Robert married Matilda (Maud) Grey, the daughter of Sir Thomas Grey of Heton and Joan Mowbray Grey. Maud Grey may have descended from king Edward I (Plantagenet) of England, born in 1289 as follows: Edward I, with his second wife Margaret had a son, Thomas of Brotherton, 1st Earl of Pembroke, born in 1300, who married Alice de Hales. Their daughter, Margaret, Duchess of Norfolk, born 1322, married John Segrave, 4th Baron Segrave. Their daughter, Elizabeth Segrave, born 1338, married John de Mowbray, who died in 1410. Their daughter Joan de Mowbray married Thomas de Grey, Baron of Hilton. Their daughter was Matilda Grey.(2)
Sir Robert and Maud had eleven children. Their son Robert, 1406, Lord Ogle of Ogle and Redesdale married Elizabeth Kirkby. Margery Ogle married R. Harbottle. Agnes Ogle married M. Whitfield. John married Margaret Booth. Elizabeth Ogle married William Heron. Jennett Ogle married John Lilburne. Constance Ogle married John Mitford. the others were Anne Ogle Lisle, Margaret Ogle Grey, Joan Ogle manners and William Ogle, 1412. William was given land in Choppington and became the progenitor of the Ogles of Choppington and Eglingham.

(1)    "A History of Northumberland, Volume III", The Northumberland County History Committee, 1896, page 193
(2)    "Ogle and Bothal", Sir Henry A. Ogle, 1902
(3)     "A History of Northumberland in Three Parts, Part II, Vol. I", John Hodgson, page 128
(4)    "A History of Northumberland in Three Parts, Part II, Vol. II", John Hodgson, page 154
(5)    "A History of  Northumberland in Three Parts, Part II, Vol. I", John Hodgson, page 52