While flying to his base alone, over northwest Egypt on 29 August 1941, Caldwell was attacked by two Bf 109s, in a simultaneous approach at right angles. His attackers included one of Germany's most famous aces, "Leutnant" Werner Schröer, also of JG 27, in a Bf 109E-7. Caldwell sustained three separate wounds from ammunition fragments and or shrapnel. His Tomahawk was hit by more than 100 7.92 mm bullets and five 20 mm cannon shells, but he shot down Schröer's wingman, and heavily damaged Schröer's "Black 8", causing Schröer to disengage. On 23 November, Caldwell shot down an "Experte", "Hauptmann" Wolfgang Lippert, "Gruppenkommandeur" (Group Commander) of II./JG 27, who bailed out. Lippert had struck the stabiliser and following capture had his legs amputated but 10 days later, a gangrene infection set in and he died on 3 December. For this action, Caldwell was awarded the Distinguished Flying Cross. Caldwell claimed five Junkers Ju 87 ("Stuka") dive bombers in a matter of minutes on 5 December. For this he was awarded a Bar to his DFC. His report of that action reads: