[2] Woollcombe originally served with the 1st Devon Militia,[4] before obtaining a Regular commission in the 46th (South Devonshire) Regiment of Foot in 1876.

[8] He was Deputy Assistant Adjutant General for Musketry in Bengal from 1890 and then Brigade Major for the Chitral Relief Force in Buram in 1895.

[8] He then served on the North West Frontier in India becoming Assistant Adjutant General of the Mohmand Field Force in 1897.

[11] On the outbreak of the First World War he was appointed General Officer Commanding-in-Chief of Eastern Command until 7 June 1915 when he became GOC-in-C of 2nd Army, Central Force.

The younger son was killed in action while serving with his father's regiment, the King's Own Scottish Borderers, at the Battle of La Bassée on 12 October 1914.