It probably says something of the nature of imperialism that the countries of the British Empire have flourished in the sports of cricket and Rugby Union  rather than the Association game. 

India is not a nation that one readily associates with football. It is, however, the home of two of the oldest competitions in world football.

Nagendra Prasad Sarbadhikary introduced the game to India in 1877, founding a club at Hare School in Calcutta (Kolkata).

In 1888 The Durand Cup was introduced- a tournament for British Army teams. The Royal Scots Fusiliers won the inaugural Durand cup  at Simla, beating  the Highland Light Infantry  2-1. The competition effectively  became the Indian domestic cup after World War 2. During the period we cover it was a very British affair.

The Indian Football Association was formed in 1893, and the first edition of the IFA Shield was played that year. 

Early Indian football was dominated by colonists, and the first IFA shield was won by The Royal Irish Rifles.

Barefoot- Mohun Bagan, 1911.

In the 1911 IFA Shield tournament final Mohun Bagan defeated the East Yorkshire Regiment. In front of a reputed 80000, Mohun Bagan  became the first Indian winners of the Shield, and probably the first Indian (or Asian) team to defeat European opponents.

Calcutta Football League, which kicked off in 1898, is the oldest league in Asia. The Gloucestershire regiment won the first title. Calcutta FC won in 1899 and in the seasons up to 1937 British military outfits won the league 29 times, punctuated by 8 Calcutta FC wins.  In 1934 Mohammedan Sporting Club began a 5 season sequence of wins.