When you're doing both, should you use a roller to massage your muscles first, stretch first, or does it not matter?
My routine includes trying to do this twice a day which includes after running, biking, etc.
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Stretching is still debateable as a need anyway, and the only study I'm aware of on foam rolling shows it to have short term benefits but not much in the long term. Neither is proven critical to athletic performance. Full range-of-motion activities however do tend to increase flexibility and strength throughout that range.
So combining two things with clinically debatable value and then trying to figure out which should come first is fairly subjective.
If your goal is to feel good afterwards then do whatever feels the best. From a practical perspective I see most folks foam rolling at the gym and stretching is something you can do throughout the day after the fact.