Yes, it matters.
Use the controlled feed Winchester for everything if you have the choice to do so.
The fellow I will be hunting Africa with at the end of this month just broke the bolt handle off of his .300 Mag Remington Sendero when a case stuck in the chamber. He did this barehanded on the firing range, no tools required.
He has decided since then to acquire some Winchesters for our hunt. Thank God.
Consider that before you go afield with a rifle that sports a two piece bolt and a push feed system....