Preheat the oven to 400°F. Cut and deseed the delicata squash. Cut one squash into small slivered pieces, and leave the other in 2 halves. Roast in the oven for 18-24 minutes, or until the halves are fork tender and the slivered pieces are golden on the bottoms.
While the squash is roasting, prepare the rest of the recipe. Halve the tomatoes and finely grate the garlic.
In a large dutch oven on medium heat, add the olive oil. Add the tomatoes and season with salt. Cook down for 1-2 minutes, the tomatoes will immediately begin to break down into a sauce.
Add in the garlic and red pepper flakes and continue to cook for another 4-6 minutes, stirring occasionally. Toss in the basil and stir again. Reduce the heat to low and continue to stir every few minutes or so.
Start the cavatelli pasta. Bring a large pot of water to boil, generously salt it, and boil the pasta for about 7-8 minutes.
At this time, the squash should be done. Scoop out the squash from the two halves and blend it with 1/2 cup of water until smooth. Add this to the pasta sauce, stir and season.
When the pasta is done cooking, use a slotted spoon to scoop it in to the tomato sauce. Stir to combine, adding pasta water as needed to keep the sauce smooth and glossy.
Add the delicata squash pieces and stir again.
Serve warm with black pepper and basil to garnish!