He tacitly witnessed his government launch an invasion of Kashmir from the frontier tribal areas adjoining the NWFP, and then oversaw it under directions from Governor-General Muhammad Ali Jinnah.

Cunningham served as the governor of the North-West Frontier Province three times, twice during the British Raj[4] and once after the creation of the Dominion of Pakistan.

However, he was invited by the colonial government in July 1947 to return and resume the office at the request of Pakistan's incoming governor-general Muhammad Ali Jinnah.

An All-India Muslim League ministry headed by Abdul Qayyum Khan Kashmiri was appointed on 23 August.

[5] In the subsequent months, the Pakistani tribal invasion of Kashmir was carried out under the nose of Cunningham, orchestrated by the provincial premier Abdul Qayyum Khan along with the Muslim League National Guard commander Khurshid Anwar.

But he fell in line after the accession of Kashmir to India, when Jinnah ordered his governors to enter into "the full spirit of the struggle".

His diary entry states, "I could have found half a dozen excellent grounds for resigning in the last two weeks or so, but I feel that we may be able to get the thing gradually under control again and that one must try to see it through.

Partnered with Louis Greig in his favoured half-back position, Cunningham ended on the losing side after a narrow 6-5 win by the Welsh.

The next season Cunningham was back in the Scotland team and played in the first game of the 1909 Home Nations Championship, again facing Wales.