Private Isherwood had been born in Radford, Nottinghamshire but later lived in Sheffield. His parents, William and Hannah, both originated from the Stockport area and, at the time of the 1901 Census, Stephen had moved to Cheadle Hulme and was living with his uncle, John Isherwood, at 83 Hulme Hall Road.
He had attended Cheadle Hulme Wesleyan Sunday School. His ambition, from an early age, had been to be a postman. He started work as a telegraph messenger at Cheadle Hulme Post Office. He stayed in this position until he was 20, when he became postman at Bramhall. After some time, he transferred to Reddish, Stockport. He was there for about 8 years before returning to Bramhall. In 1913, he married Alice Georgina Waters in a civil ceremony registered at Stockport . They set up home at Grove Lane, Cheadle Hulme and would have two children together.
He enlisted in May 1916 at Stockport, later training at Litherland Camp, Liverpool. He had only been at the front for a short time before he was killed. The last draft of replacements joined the Battalion in November 1916, so it is probable Stephen was with them. This month was spent at Amara, undertaking various training exercises. Amara is now a town of some 200, 000 people in south eastern Iraq. During the war, it was a major hospital and rest area for the troops fighting in Mesopotamia
On 28 November, they left camp and moved towards the front line near Sinn Abtar and Bassouia. On 20 December, there was an attempt to cross the River Tigris, but this seems to have been half-hearted as minimal Turkish sniper fire seems to have deterred the whole Division and orders for a withdrawal were given. Christmas Day was spent in the front line. It was reported that there was intermittent enemy artillery which did no real damage. During the night, a patrol was sent forward some 2000 yards but there was no sign of the enemy positions. On 30 December, 40th Brigade was withdrawn from the front line and returned to reserve camp at Bassouia.
The War Diary records that the first week of 1917 was spent in "straightening out" the Battalion after it had been constantly on the move for over a month. Fatigue parties worked daily cutting brushwood to make a road. On 12 January, the period of "rest" was over and the Fusiliers were ordered back into the front line to prepare for an attack on the Turkish positions. On arrival, they found that there was no real trench network and digging started immediately. At this point, the Turks were only 350 yards away, across flat ground with very little cover. They were able to continually snipe at the British troops. But, by 24 January, the work was complete and a proper front line, 1200 yards wide, had been prepared, together with communication trenches to the rear area. A total of 5 miles of trench had been dug and 8 men had been killed
The attack took place next morning, with the Fusiliers assaulting a 500 yard wide section of the enemy trench. The attack was success, although there were a number of casualties during the charge across No Man's Land. As soon as the position had been taken, Captain Farrar (the officer in charge of the attack) reorganised the troops and pushed forward some soldiers, whilst others consolidated the gains. Whilst the consolidation was underway, the other men had captured the Turkish second line of trenches. By dusk, consolidation was complete and preparations were in hand for a further advance the next day. By that time, Stephen and 26 other men had been killed. Amongst the 26 were two other local men, William Jones and Walter Cooke. Joseph Holland had been badly wounded and died later the same day.