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On the morning of the 18th June whilst the French drew into battle array the 27th marched from Waterloo down the Brussels Road to their reserve position 100 yards from the Farm at Mont St Jean. By 3 o'clock in the afternoon the situation was critical. Wellington had held the first major French attack, but lost most of his heavy cavalry. The second huge French infantry attack was underway up the Brussels road to capture La Haye Saint farm complex and punch through the British centre. The 10th Brigade were ordered up to the crossroads in the centre of the allied line, the 27th led with the 4th and 40th in support.
During the next five hours the Regiment held the crucial crossroads position, sometimes in square formation to meet cavalry, sometimes in line to make maximum use of their firepower. Throughout the period they were under continuous fire from all types of French fire from caronnades to snipers. About 6 o'clock as the huge French cavalry attacks were taking place between the crossroads and the top of the hill some 500 yards to the west. The Officer Commanding the 40th noted that there were no officers, except Captain O'Hare left alive in the 27th. He came forward and offered to loan some of his own officers to the regiment. O'Hare rejected to offer with the comment that, " sergeants of the regiment liked to command the companies, and he would be loath to deprive them of the honour".
Later, as the battle turned, and with the sun going down, Wellington gave the signal for the general advance from a position just to the east of the Inniskillings. For 5 hours they had endured a grim encounter. They had neither advanced nor retired. For much of the time they had been pounded by enemy artillery, and between times had fought off French cavalry and infantry who sought to break them. Of the 720 officers and men who went into the battle 470 were killed or wounded. No other regiment under the Duke's command suffered so grievously.
Napoleon himself stated, " the day was won. The army had performed prodigies; the enemy beaten at every point: only the English centre still held".