Preheat the oven to 425° F.
Place the squash on a cutting board and with a chef's knife cut a tiny sliver off the squash from the side. Cut the squash in half across (not lengthwise), scoop out the seeds and discard. Season the cut sides with salt, black pepper, and 1 tablespoon of olive oil. Place the 2 smashed garlic cloves with the paper skin on the sheet pan and place each squash half, cut-side down directly over the garlic. Transfer the pan to the oven, and roast for 40-50 minutes until the flesh is soft when pierced with a fork or knife. Remove from the oven and allow them to cool before raking the strands with a fork. If the squash has excess moisture, then place the squash noodles in a colander or strainer and rest for 10 minutes.
Heat large skillet on medium-high heat. Add remaining olive oil to pan; swirl to coat. Stir in remaining chopped garlic, tomatoes, crushed red pepper flakes, and sugar. Cook 6-8 minutes until tomatoes start to pop. Add arugula, lemon zest + juice, and continue to cook for 2-3 minutes. Season with salt and pepper, to taste; add squash noodles, fresh basil, and pine nuts. Lightly toss all ingredients and finish off with feta and parm. Enjoy!