The Y on the football sweater stands for Yale University. At the time, its football team was a collegiate powerhouse.
This was the first Popeye cartoon in which he doesn't eat spinach. (Olive eats it instead.)
Sports were becoming more mainstream in the 1930s, thanks, in part, to their being broadcast on radio and shown in cinema newsreels.
One of a number of Popeye shorts sent to Asia in the 1980s to undergo a redraw and colorization process.