The squadron returned to North Africa. On 26 June 1941, while escorting bombers attacking Gazala, Libya, Caldwell destroyed an aircraft in air-to-air combat for the first time, during his 30th sortie. He downed a German Messerschmitt Bf 109E, piloted by "Leutnant" Heinz Schmidt of I gruppe, "Jagdgeschwader 27" (JG 27—Fighter Wing 27), over Capuzzo, he followed this claim with a 'half share' of a Bf 110 on III./ZG 26 and 2 Ju 87s of II./"Sturzkampfgeschwader 2" (StG 2—Dive Bomber Wing 2) on 30 June.