Season 2 pounds of chicken breasts with 1 teaspoon kosher salt, ¼ teaspoon black pepper, and 1/2 teaspoon dried oregano.
Preheat a 12-inch ovenproof skillet (preferably cast iron) skillet over medium-high heat for 3 minutes, then warm 1 tablespoon olive oil for 30 seconds. Sear chicken for 3 to 4 minutes per side, until golden brown. Transfer to a cutting board.
Reduce skillet heat to medium-low and add the remaining 1 tablespoon olive oil. Cook 4 diced garlic cloves, ⅛ teaspoon red pepper flakes and remaining 1 teaspoon dried oregano for 30 seconds, until fragrant.
Carefully pour 14 ounces tomato sauce and 14 ounces diced tomatoes into the skillet (it may splatter, beware!). Stir in half (8 ounces) of the halved cherry tomatoes, 1 large basil spring, 2 bay leaves (if you have them sitting in your cabinet), and ½ teaspoon kosher salt.
Preheat oven to 400°F.
Cook over medium-low heat for 10 minutes or until sauce is thickened.
Nestle chicken breasts down into the tomato sauce and transfer skillet to oven.
Cook for 10 to 12 minutes. Use an internal thermometer to check the chicken temperature at the 10 minute mark. Pull it out when it reaches 155°F (we aren’t finished cooking it yet!).
Change the oven temperature to broil (on high if your oven has broil settings).
Transfer skillet to stove top and evenly distribute 4 to 6 ounces mozzarella and about 10 pepperoni over top. Add whatever other pizza toppings you love!
Broil for 2 to 3 minutes, until the pepperonis are lightly crispy and the cheese is melted.
Meanwhile, make the zoodles by slicing the zucchini in half vertically, but leaving it attached at the stem. Holding the zucchini by the stem, use a vegetable peeler to peel the zucchini into wide zoodles. Divide zoodles between 4 bowls.
Once the cheese is melted and pepperonis are a bit crispy, remove the skillet from the oven and scatter the remaining 8 ounces cherry tomatoes and ¼ cup thinly sliced basil leaves over top of the pizza chicken.
Fish out the basil sprig and bay leaves to discard them as you serve!
Serve pizza chicken and sauce over the zoodles.