[1] Calcraft entered the army as a cornet in the 15th Light Dragoons in March 1788, and was promoted lieutenant in 1793; in that year his regiment was ordered to join the force under the Duke of York and Albany in Flanders.
All the eight officers of the 15th present there were knighted, and received the Order of Maria Theresa from Leopold II, Holy Roman Emperor.
[2] In 1799 Calcraft accompanied Henry William Paget, who commanded the cavalry brigade in the Anglo-Russian invasion of Holland, as aide-de-camp; he was wounded at the Battle of Alkmaar on 1 October, and was for his services promoted major into the 25th Light Dragoons in December 1799.
[2] In 1807 Calcraft was elected Member of Parliament for Wareham, but resigned his seat at the close of 1808 on his regiment being ordered for service in the Iberian Peninsula.
General Fane fell ill, and Calcraft assumed the command of the Brigade, which he held until the arrival of George de Grey in May 1810.
The Brigade was then engaged in covering Rowland Hill's retreat from Madrid, and in December 1812 Calcraft was made a knight of the Portuguese Order of the Tower and Sword for his services.