Heat the oil in a large skillet over medium heat. Add the onion, carrot, celery, and oregano and cook, stirring occasionally, until slightly softened, 4 to 5 minutes. Add the beef and garlic and cook, breaking the beef into smaller pieces with a wooden spoon, until the onion and beef are lightly browned, 9 to 10 minutes. Pour in the wine and cook until it is nearly evaporated, 1 to 2 minutes. Add the crushed tomatoes, tomato paste, and zucchini; bring to a simmer and cook, stirring often, until slightly thickened, 2 minutes.
Stir in the rigatoni, salt, pepper, and 3 cups water; bring to a simmer and cook, stirring often, until the sauce is somewhat thickened, about 18 minutes. Add 1 cup water and continue cooking until the pasta is tender, 9 to 10 minutes more.
Serve the rigatoni topped with the Romano and basil.
