Slice squash in half length-wise and brush both sides with 2 tbsp olive oil. Place squash cut side down on a baking sheet and roast in the oven for 45 minutes.
After 30 minutes of the squash roasting, prepare the rest of the meal. Heat the remaining 2 tbsp olive oil in a large skillet over medium heat and add the tomatoes. Cook tomatoes for a few minutes, then add the garlic and stir. Continue cooking until tomatoes are blistered on both sides.
Pour sauce into the same skillet and heat it up until it's at your desired temperature. Stir in the oregano and red pepper flakes.
Once squash is done cooking, use your fork to pull back a few spaghetti strands, then divide the garlic, tomatoes and tomato sauce mixture between both sides of spaghetti squash. Add the burrata cheese on top, then add more red pepper flakes if desired.