MacGregor took off at dawn in a Tomahawk and reported a large concentration of tanks before his aircraft was hit by anti-aircraft fire over 'Knightsbridge'. The shell exploded in the wing root, but he was able to return.
On 11 June, Bir Kakeim fell and reconnaissance sorties identified very large enemy concentrations in the 'Knightsbridge' area. MacGregor was over the area when four BF109s attacked him. His Tomahawk was hit repeatedly by canon fire, but he manged to reach the El Adem area with his assailants behind him. The aircraft caught fire and he crash landed, after which the BF109s strafed the burning wreckage. MacGregor was fortunate to sustain only minor injuries and, during the engagement, he claimed to have hit one of the enemy fighters, which dived away trailing black smoke.
In July 1942, there was a need to reorganise the Squadron's three flights following the loss of many pilots, and the now Flight Lieutenant MacGregor was appointed as a Flight Commander. Always seemingly to be in the thick of battle, he had to make another forced landing in the desert on 8 July after completing a Tac R in the northern area. His weaver saw him go down, and he was soon picked up. He had never shirked a fight and his service was recognised with the of the DFC, the citation concluding: ' This officer has displayed high courage and great devotion to duty in the face of the enemy.'
On 24 August 1942, a last-light reconnaissance was requested to investigate some reported enemy movements. MacGregor ad a colleague took off, but nothing further was heard from either of them. Many months later it was learned that both were prisoners of war.
MacGregor must have had more adventures than any other wartime 208 Squadron pilot. He was shot down twice by fighters and twice by anti-aircraft fire. On a fifth occasion, his Tomahawk was badly damaged by anti-aircraft fire but he managed to get back to an advanced landing ground. During his reconnaissance sorties he had fought some of his assailants and had been credited with probably destroying one and damaging a second. There can have been few DFCs more merited.
Rob Pinnell takes up MacGregor's story following his disappearance on 24 August 1942:
Robert was captured when he was shot down in flames and crash landed behind enemy lines. The hood of the cockpit was jammed shut with the inferno engulfing him but the brave German soldiers grabbed axes and smashed their way through to rescue Robert.
He repaid them by later escaping. He was recaptured and tortured by an Italian officer with big and heavy alpine boots and being held in a cage measuring 5ft by 3 ft. He was aided by some black Rhodesian POWs who smuggled him food.
