The British Indian Army garrison stationed at Fort William played an instrumental role in shaping the Calcutta Football League by putting forth numerous teams alongside other European settlers.

[10][11] 1921 saw the rise of East Bengal who began their CFL journey in the Second Division in place of Tajhat Club who had withdrawn from the league.

At this, the club called for amendments and in the following General Meeting of IFA, the nine British teams conveyed their approval, while Mohun Bagan and Aryan opposed it.

The rapidly increasing off-the-field rivalry between the respective fans of Mohun Bagan and East Bengal saw one of the darkest days of Indian football when 16 fans lost their lives because of a stampede and rioting during a Kolkata Derby in CFL on 16 August 1980 in Eden Gardens.

The importance of regional competitions decreased as all the top clubs in the state were racing for the national honours.

From the later 20th century, Mohammedan eventually lost its stronghold and, Mohun Bagan and East Bengal became the only dominant teams in the league.

Starting in 2010, East Bengal won a record eight consecutive titles until their arch-rivals Mohun Bagan broke the streak in 2018.

In 2018, the league's popularity had a sudden upsurge and recorded more than 15,000 spectators even in matches involving small clubs.

Small clubs like Peerless and George Telegraph introduced some of the foreign talents that later went on to become big names in the country.

[10] In 2019, Peerless clinched the honour and became the second team outside the Big Three after Eastern Railway to win the league since 1958.

[6] ↑promote (I-League 3) ↓relegate 3 ↑promote 2 ↓relegate 2 ↑promote 2 ↓relegate 2 ↑promote 2 ↓relegate 2 ↑promote 2 ↓relegate 2 ↑promote 2 ↓relegate 2 ↑promote 2 Starting from 2023, 26 teams participate in the Premier Division, divided into two groups at the same pyramid level and compete in a single-leg round robin tournament.

The most successful clubs participating in the top-tier of the league includes East Bengal, Mohun Bagan and Mohammedan.

Top three teams from the two groups shall proceed to the championship round, where each play five more matches to determine the champion.

The list only contains the names of the teams that have won the top-most division of the Calcutta Football League more than once.