All that is known of Cunningham's earlier military career is that he held a commission in the Scots Brigade in the service of the Dutch Republic, that he was present at the Battle of St. Denis in 1678 and was wounded there.
This regiment fought at the Battle of Killiecrankie[1] on the extreme left with his second, Lieutenant-Colonel Lauder, both were abandoned by their men and Brigadier-General Balfour was killed.
In December 1688 Cunningham obtained a majority in the Earl of Arran's Regiment of Cuirassiers.
In 1689 his services were rewarded by the Colonelcy of a Regiment of Foot which was modeled out of the existing forces in Scotland.
Cunningham remained in command until he was promoted to the rank of brigadier at Mariekirk on 1 June 1696.