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Preheat the oven to 475 ̊. Whisk the olive oil, Worcestershire sauce, ranch dressing mix, black pepper and salt in a large bowl until combined. Transfer 3 tablespoons to a small bowl and set aside for brushing.
Add the squash, zucchini, bell peppers and red onion to the large bowl with the marinade and toss until coated.
Spread out the vegetables in an even layer on a sheet pan. Bake until softened and golden brown in spots, about 30 minutes.
Meanwhile, place the pork chops on a second sheet pan and brush both sides with the reserved marinade. Sprinkle one side with the paprika. Toward the end of the vegetable roasting time, add the pork to the oven and cook until no longer pink in the middle, about 7 minutes. Sprinkle the pork and vegetables with the parsley.