The first version of the Elmwood Casino was located in the same spot. Opened in the early 1920s as the Elmcourt Tennis & Country club. Later on during the depression years, in 1934, the Elmwood Hotel opened in the old clubhouse of the Country Club.
By the early 1940s, the supper club format was underway. In December, 1943 the original Elmwood burned to the ground. When the fire broke out, responding fire trucks were held up by trains at the tracks on Dougall Avenue. A replacement building got underway shortly after, however during WWII materials were scarce and the building on Dougall was subject to stop work orders in 1944 for building with steel.
Backlash ensued, and the owners sold their stake in 1946, when the new Elmwood was taken over Al Siegel. Siegel was the one responsible for making the Elmwood the entertainment hot spot it became, until the end of 1974, when the operation filed for bankruptcy.