The Railway Cup is an annual competition involving the top four teams in the Canada Life Premier League at the halfway stage. The final is played on Boxing Day. In 2020, Corinthians beat Rushen 1-0 to claim the trophy.

This season sees the 103rd playing of the Railway Cup, which was first presented to the Isle of Man FA by the Isle of Man Railway Company in 1905. 

Ramsey and Gymnasium reached the first final in 1906, which the Association set down for a Saturday. The northerners (who played home games on Thursday) objected strongly to the final being arranged for a Saturday and in the end the trophy was awarded to the Tromode side. The following year Gymns reached the final again and retained the trophy after beating Castletown 1-0 in a replay.

By the time the original was replaced in 1925 by the magnificent trophy at stake today - one of the largest in European domestic football - Ramsey had won the  cup a record four times.

The format for the trophy has changed over the years as it was originally open to all Association members but in 1936 the present format was adopted, with the top four teams in the top flight, at the half way stage, contesting the semi-finals. At one time the Railway Company was heavily involved in the running of th e competition and helped select the venues for the semi-finals. Any involvement by the company in the organisation of the competition ended in 1952.