Irish alliance Kingdom of England The Battle of Deputy's Pass was fought in County Wicklow on 29 May 1599, during the Nine Years' War in Ireland.

A Gaelic Irish force under Felim McFiach O'Byrne ambushed an English army of about 500, under Sir Henry Harrington, which was marching from Rathdrum to Wicklow.

When Robert Devereux, 2nd Earl of Essex was appointed Lord Lieutenant of Ireland in 1599, he ordered Harrington into County Wicklow to deal with the O'Byrnes and their allies, the O'Tooles.

Captain Atherton, the Sergeant-Major of the army, had little doubt that the weight of any Irish attack would fall on the rear of the column.

The army had marched little over a mile before the Irish shot (musketeers and caliver-men) began skirmishing with the rear of Harrington's force.

[5] Again the English shot secured the crossing, as Irish fire slackened, possibly due to a shortage of gunpowder.

The Irish brought up a stand of pikemen, but their attack was limited to the English left, as the right of the column was shielded by thick gorse bushes.

Without the support from their shot, Atherton's men refused to charge the Irish, then withdrew to the main body of the English column.

Montague's English cavalry charged to support the panicking infantry, but the Irish pike square opened, allowing the horse to pass through.