Although planting fall rye on summerfallow and winter wheat and winter triticale on chem-fallow is a recommended practice, this article is entirely focused on stubble planting as I am not a fallow enthusiast. While the exact date varies by location, September 1 is a good planting date to shoot for over most of Saskatchewan. Having a field ready in time might happen by accident but it happens a lot. It's better if it isn't left up to chance. That means seeding the spring crop early and planting crops that will mature in time.
Good choices are barley and Polish canola sown first thing in the spring.
The time management doesn't stop with crop selection. It also helps to arrange your spring planting so harvest is staggered somewhat. If your early maturing crop is sown early in preparation for winter cereal seeding and then you move to a later maturing crop, you can end up with a window of time during harvest to plant your winter cereal. The next step in managing time for winter cereals is to get your seeding equipment ready for seeding immediately after seeding. Now that's not a type-o.