The 1944 VFL season was the 48th season of the Victorian Football League (VFL), the highest level senior Australian rules football competition in Victoria.

All twelve of the league's clubs competed, with Geelong returning after two years in recess due to wartime travel restrictions.

The premiership was won by the Fitzroy Football Club for the eighth and final time in its history, after it defeated Richmond by 15 points in the VFL Grand Final.

The determination of the 1944 season's fixtures were greatly complicated by the fact that, although the Western Oval and the Junction Oval were now available to the VFL, the Melbourne Cricket Ground and the Lake Oval were still appropriated for military use and, because of this, Melbourne was sharing the Punt Road Oval with Richmond as its home ground, and South Melbourne was sharing the Junction Oval with St Kilda as its home ground.

Once the 18 round home-and-away season had finished, the 1944 VFL Premiers were determined by the specific format and conventions of the Page–McIntyre system.