The Coolavokig ambush (Irish: Luíochán Chúil an Bhuacaigh) is carried out by the Irish Republican Army (IRA) on February 25, 1921, during the Irish War of Independence. It takes place at Coolavokig, on the road between Macroom and Ballyvourney, County Cork. A 60-man flying column of the IRA’s 1st Cork Brigade under Seán O’Hegarty, ambushes a 70-man convoy of the Auxiliary Division under Major Seafield Grant, sparking a four-hour battle. Ten Auxiliaries are killed, including Major Grant, and others wounded. The IRA column leaves the area when British reinforcements arrive. After the ambush, British forces stop carrying out raids and patrols in the area.

The IRA flying column had been attempting to ambush the Auxiliaries for two weeks but had always missed them. As they occupy the ambush position over a few days, their position becomes known and a force of seventy Auxiliaries and seven Royal Irish Constabulary (RIC) constables move against them, heavily armed with rifles, machine guns and grenades. The sixty-two IRA volunteers include units from the 1st, 7th, and 8th battalions of the 1st Cork Brigade, and are divided into four sections. Apart from commander Seán O’Hegarty, the main IRA officers are Dan “Sandow” O’Donovan and Dan Corkery. The IRA is armed with sixty rifles, several shotguns and revolvers, and two Lewis guns, but significantly, no grenades. The British forces, traveling in eight lorries and two cars, also carry four Irish hostages with them.

Around 8:00 a.m. on February 25, IRA scouts signal the approach of the British force. The British are forewarned about the IRA position however, and approach with caution, when a republican leaving his post turns to run back and is seen from the leading lorry. When half of the lorries come into the ambush position the IRA opens fire. According to An Cosantóir, one lorry immediately turns around and speeds back to Macroom.

Rifles and a Lewis machine gun from the IRA’s No. 1 section, and ten rifles from the No. 4 section, open fire, as they are the only republican units that have a field of fire on the lorries. They then drop to the ground to avoid return fire. Sections No. 2 and No. 3 swing around to the east, on a hillside, in an attempt to encircle the British northern flank, but they can get no closer than 500 yards.

The Auxiliaries are quickly losing ground and taking casualties. Major Grant is killed while rallying his forces. The British forces retreat into two nearby cottages. The IRA closes in and as they are preparing to bomb the cottages, large numbers of RIC reinforcements approach and begin encircling the area. After fighting a half-hour rear guard action, the IRA flying column retreats toward the northwest. The engagement at Coolavokig lasts four hours, until soldiers of the Manchester Regiment arrive.

It later transpires that the Auxiliary forces are just part of a large round-up operation planned for that day which includes 600 British Army troops from Cork, Ballincollig, Bandon, Clonakilty, Skibbereen, Bantry, Dunmanway, Millstreet, Macroom, and Killarney. After the ambush, British forces cease raiding and patrolling the area west of Macroom, effectively handing it over to IRA control. They are reluctant to enter the area and only do so later with a strong force of 2,000 men.

The IRA suffers no casualties. However, the number of British casualties has been disputed to this day. The British claim that only Major (Auxiliary Commandant) James Seafield-Grant was killed during the ambush, and that two other Auxiliaries later died of their wounds. The IRA claims that between 14 and 16 members of the British force were killed. The Digest of Service for the 1st Battalion, Manchester Regiment, records that on March 18, 1921, a party proceeds to Coolavokig to destroy houses believed to have been used by the IRA.