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Oliver at Solway Moss, October 1542

Oliver Sinclair was, according to Baronage Press, one of the Sinclairs
of Haddingtonshire. According to what I have just finished, "The Border
Reivers" by Keith Durham, published by Osprey Press, Oliver was "The
King's (Scot's James V) hated favorite. When he was put in temporary
command of a force of 15-18,000 men, the other Scottish commanders
hostility and dissention caused the loss of the battle.
When attacked by Thomas Wharton, Deputy Warden of the English West
March, with a force of about 3,000, they caught the Scots fording the
river Esk. The Scots were caught between the banks of the river and the
Solway marsh. Wharton deployed between 700-800 men to "maul the Scottish
right flank". The Scots commanders were in dispute amongst themselves as
to what to do. Confusion took hold among the Scottish and then a growing
panic caused by the ferocity of the English attack.  Discarding
standards, cannon and handguns the Scots began a disorderly retreat.
Among the 1200 prisoners taken for ransom was Oliver Sinclair.  It is
interesting that the fleeing army was again mauled by their own
borderers, the Grahams and particularly those of Liddesdale plundered
the shattered army making pursuit by the English unnecessary. Certainly
no honour among theives!(borderers) The Sinclairs of the area below
Edinburgh were also considered in Border lands (Middle March)

Oliver St. Clair, 12th Baron of Rosslyn
 1484   b.c. 1456 d. 1511-1523
 m. 1st Christine Haldane
 m. 2nd Elizabeth d/o Lord Borthwick
 m. 3rd Isabella Livingstone
William ,
Henry Bishop of Ross
Oliver of Pitcairns and Whitekirk, (maybe or maybe the next one)
John Bishop of Brechin and Lord President of the Court of Sessions,

 William, 13th Baron of Rosslyn; died before 1554
  endowed Rosslyn Chapel
 m. Alison Hume d/o George Lord Hume.
 Ch: William, Gilbert, Patrick, Alexander of
 Cuthilton and Little Denny, John, Oliver of
 Westravensneuk, Sir Mathew, Edward of
 Dryden and Ethay.
Since I don't have dates for these Olivers, Ian or Niven would be the
best to answer.
They would most probably be "Herdmanstoun" area Sinclairs.