Today the Ottawa region is administered by Hockey Eastern Ontario (HEO).

In the early days, the OCHL had a relationship with the geographically larger Ontario Hockey Association (OHA), which also formed in 1890.

After the OCHL's Ottawa Hockey Club won its third consecutive OHA championship, Lord Stanley signaled the creation of today's Stanley Cup by sending the following message to the victory celebration held on March 18, 1892, at Ottawa's Russell Hotel:[4][5][6] I have for some time been thinking that it would be a good thing if there were a challenge cup which should be held from year to year by the champion hockey team in the Dominion (of Canada).

There does not appear to be any such outward sign of a championship at present, and considering the general interest which matches now elicit, and the importance of having the game played fairly and under rules generally recognized, I am willing to give a cup which shall be held from year to year by the winning team.

[5] Ottawa HC repeated as OCHL and OHA Champions in 1893, and competed in the challenge-based, rather than schedule-based, Amateur Hockey Association of Canada (AHAC).

The AHAC's Montreal Hockey Club defeated Ottawa HC in a mid-season challenge, and were awarded the first Stanley Cup.

In 1919, in a ruling from the CAHA, the rival Capital HA's CCHA teams were forced to join the OCHL, ending the feud that had caused the dissolution of the AHAC in 1898.

During World War II, the league admitted senior teams from the armed forces stationed at Ottawa.

The famous 'Kraut Line' of the Boston Bruins played for the Ottawa RCAF Flyers and won the Allan Cup.

Many famous players have graduated from, or played in the league, including Punch Broadbent, Eddie Gerard, King Clancy, Bill Cowley, Syd Howe, Aurel Joliat, Frank McGee, Ken Reardon and Milt Schmidt.

of Ottawa 1936–37 Rideaus 1937–38 Primrose 1938–39 Hull Volant 1939–40 New Edinburgh 1940–41 Canadiens 1941–42 Univ.