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.
Stretch first then massage or roll out your muscles.
Stretching will loosen up your muscles some to allow the massage to get in deeper and help blood circulation or break up stuff that needs to be cleaned out by the blood.
I can confirm from first hand experiences that stretching will prevent your muscles from healing in a tight manner. Also that massaging can help break up "knots". I think that the debate that Eric mentions is mostly addressing whether or not it is necessary which is different than saying whether or not it helps.
J. Doe does have a point too. Generally things that are healed better by stretching are not good or even made worst by massaging, and the same for things healed better by massaging - like knots. Massaging without stretching is difficult and requires more time and effort to soften up the muscle before getting in deeper. Similarly an extra tight muscle shouldn't be massaged.