As a corporal in 4 Platoon, B Company, 3rd Battalion, The Parachute Regiment, he won the Military Medal for bravery during the Falklands War of 1982.
During the Battle of Mount Longdon on 12 June 1982, 4 Platoon's Commanding Officer, Lieutenant Bickerdyke, along with Sergeant Ian McKay, a signaller and several other paratroopers went forward to reconnoitre the enemy positions.
[1][2] Bailey later said of the attack on Mount Longdon: Ian and I had a talk and decided the aim was to get across to the next cover, which was 35 metres away.
He shouted out to the other corporals to give covering fire, three machine-guns altogether, then we – Sergeant McKay, myself and three private soldiers to the left of us – set off.
He was also shot in the neck and the bullet severed the cord holding his identity tags; they were found in 1983 during a de-mining operation.
[4] Bailey later reached the rank of warrant officer class I and was commissioned as a captain in the Parachute Regiment on 6 April 2000.
In November 2009 it was reported in the British media that he intended to sell his Military Medal group because he was unable to work following further surgery in 2009 to remove shrapnel from his hip left from his 1982 injuries.