"Illustrious" left Scapa Flow in August and arrived in the Mediterranean by September. Orr became an ace in the following months, claiming seven aircraft shot down out of 30 claimed by his squadron. Orr's victories included a CANT Z.501 flying boat on 2 September and on 4 September off the Dodecanese he shared in the shooting down of a Savoia-Marchetti SM.81 bomber. One of the first larger missions Orr took part in was providing the fighter cover for the Fairey Swordfish attack on the Italian fleet at Taranto. Other missions included attacks on German army positions at Bardia, bombing Tripoli in Libya, and attacks on the Rhodes airfields. Orr was also awarded his first Distinguished Service Cross (DSC) for his service during these missions.