Battle of Clontibret The Battle of Clontibret was fought in County Monaghan in March 1595 during the Nine Years War , between the crown forces of England ' s Queen Elizabeth I and the Irish army of Hugh O ' Neill , 2nd Earl of Tyrone . It ended in victory for Tyrone , and was the first severe setback suffered by the English during the war . Background . The Nine Years War began with a conflict over English efforts to maintain a string of garrisons along the southern border of Tyrone ' s territory in Ulster . The Irish leader promptly besieged the English garrison at Monaghan Castle , and Sir Henry Bagenal , commander of the English forces , marched out to its relief on 25 May ( 4 June New Style ) from Dundalk , via Newry . His army was made up of 1 , 750 troops , including some veterans and certain companies newly arrived from the Spanish campaign in Brittany , but there were many recruits in the ranks . Bagenal ' s men were predominantly infantry , armed with muskets and pikes ; there was also a small number of horsemen raised in the Pale . The battle . The Battle of Clontibret was essentially a two day running fight , as Bagenal ' s column was ambushed on its way to and from the castle at Monaghan town . The Irish fought sharply along the roads about Crossdall , around 4 miles ( 6 . 5 km ) from Monaghan , firing on the English column with caliver s ( light musket s ) from the surrounding woodland . With the loss of 12 dead and 30 wounded the English reached the castle , which was re - supplied and reinforced with one company . Bagenal had misgivings about his supply of powder and lead , much of which had been used on the way , and could afford little for the garrison before he started back . Two days later , on 27 May , Bagenal set out for Newry in a column , but by another route , past the townland of Clontibret . The route lay through Drumlin country , which abounded with hills , bogs and woods , making it ideal for an ambush . The column came under fire from the outset , and then fell into a major ambush at a pass near Clontibret . Tyrone ' s army - about 4000 strong - consisted of contingents from the O ' Neill , MacMahon and Maguire clans , as well as Scottish mercenaries . The Irish also deployed a greatly enlarged force of cavalry and caliver - men ( musketeers ) . To Bagenal ' s puzzlement , the caliver - men were turned out in red coats and acquitted themselves with expertise . Fire from the flanks was heavy , and many English troops were killed or fell wounded while the Irish cavalry played around the fringes . Tyrone himself was almost killed in hand - to - hand combat with a Palesman named Seagrave , who led a cavalry charge on the Irish position . Seagrave had his arm chopped off by Tyrone ' s standard bearer O ' Cahan , and was killed by Tyrone with a dagger thrust to the groin . Bagenal ' s column was slowed to a crawl and , as night fell in the wilderness , the commander called his men to a halt and camped at the hilltop of Ballymacowen . It seemed that hundreds were missing , and there was fear that the Irish would renew the attack under cover of darkness . There was no further attack and , a little after first light , reinforcements from Newry arrived to relieve the column . Aftermath . According to intelligence received in the days following , Tyrone ' s failure to follow up had been caused by a lack of powder - ironic , given the state of Bagenal ' s own supplies - but the overall sense in government was of disquiet , and a bad job was made of hushing up the casualty figures . This gave fuel to the rumours of a severe defeat , and many people set greater store on the numbers put about by confederate supporters . Sir Ralph Lane , the muster - master - general , informed the queen ' s principal secretary , Lord Burghley , that " " more men were hurt and killed in that late service than was convenient to declare " " . The casualty figures for both sides vary depending on sources . Bagenal admitted only 31 killed and 109 wounded on the second day of fighting , but his losses were almost certainly higher . The Irish annals claimed up to 700 English killed . Estimates of the confederate losses vary between 100 to 400 killed . Three years later , Bagenal led an army into another ambush by Tyrone , at the battle of the Yellow Ford . The English general was killed and his troops were routed with heavy losses .