299 Squadron was formed as an Airborne Forces unit at Stoney Cross on the 4th November 1943, taking its initial strength from "C" Flight of 297 Squadron. At this time the staple aircraft available to the Squadron was the Ventura, but these were swapped for Stirlings in January 1944, and thereafter the aircrews began to train themselves in the art of glider towing and the dropping of parachutists. On the 1st March, the Squadron moved to their new home at Keevil, and as of the 5th April they began to fly Special Operations Executive (SOE) sorties to France, largely dropping arms to the Resistance. For some of these missions, which continued into May, the Squadron operated out of Tarrant Rushton, using it as a forward base.

Normandy

The first of twenty-three of 299 Squadron's Stirlings took to the air at 23:19 on the 5th June, each carrying nine supply canisters and between fifteen and twenty-one men of the 12th Parachute Battalion. Light flak was encountered over the drop zone and one Stirling was lost and a further eight damaged, resulting in the injury of a number of air crew. Nevertheless the squadron successfully deposited their troops over DZ-N, near Ranville, and returned to base. Whilst this drop had been taking place, a lone Stirling, piloted by Warrant Officer Tovell, carried out a successful Special Operation sortie to Brittany, delivering troops and supply containers.

As soon as 299 Squadron landed at Keevil, their aircraft were refuelled in preparation for the Second Lift which took to the air shortly after midday, with the Squadron towing eighteen Horsas containing troops and equipment of the 6th Airlanding Brigade. The engine of one Stirling failed after take-off and was forced to ditch its charge and return to base, however the remainder of the formation flew on to Normandy without much difficulty. Over the landing zone, however, four Stirlings were damaged, mostly superficially, when the formation came under fire from light flak and several machine-gun positions, one of which was silenced by the four Browning machine-guns of Flight Lieutenant Ellis's aircraft. On the return flight, Flying Officer Clarke's Stirling crashed into English Channel with the loss of all aboard.

On the 8th June, 299 Squadron donated six aircraft to a resupply flight to the 6th Airborne Division, however, as was typical of this period, the weather was distinctly unfavourable and the aircraft, flying in pairs for better protection, were ordered to return to base. Two of 299 Squadron's Stirlings received this message and headed for home, but the remaining four did not and pressed on to Normandy where they successfully carried out their mission. On the following night, two aircraft completed sorties in support of the SAS. A further four resupply flights were mounted by 299 Squadron, with three aircraft used on the 10th June, five on the 18th, ten on the 23rd and thirteen on the 30th. Following the end of their part in the Invasion, the Squadron returned to its SAS and SOE support duties.

Arnhem

On the 17th September 1944, twenty-five Stirlings were used to tow Horsa gliders on the First Lift to Arnhem and no losses were suffered. On the following day, twenty-two gliders were taken in, and although all of their aircraft returned to Keevil safely, many had been damaged by flak. On Tuesday 19th September, seven Stirlings towed Horsas while a further seventeen took part in a resupply flight. The Squadron suffered its first losses of Operation Market Garden on this day when a Stirling crashed after it was hit by flak, causing the petrol supplies it was carrying ignite. Five men bailed out and survived, but an RASC despatcher was killed along with three of the crew, included amongst which was the commander of 299 Squadron, Wing Commander Davis. Another Stirling was lost on Tuesday when it had attempted to make a belly landing south of the Rhine, but despite initial signs of success the aircraft suddenly somersaulted and burst into flames, although despite a few serious injuries, no one aboard died.

On Wednesday 20th, a further Stirling was lost out of the sixteen that participated, and several of these were damaged. Only eleven of their aircraft were fit to take part in Thursday's effort, and 299 Squadron's final act in the Operation came on Saturday 23rd with fourteen Stirlings delivering supplies, three of which limped back to Keevil with serious damage.

299 Squadron, equal with its neighbour at Keevil, 196 Squadron, had flown a total of one hundred and twelve sorties, more than any other squadron involved in the Operation. Their brave effort to support the 1st Airborne Division had cost them five aircraft, four lives and ten men taken prisoner. A further eighteen men had bailed out over Arnhem, but they were successfully returned to the Allied lines when the 1st Airborne Division withdrew across the River Rhine on the night of the 25th/26th September.

The Rhine Crossing

The next Airborne Operation came on the 24th March 1945, during which the Squadron provided twenty-nine aircraft to help lift the 6th Airborne Division to its drop zones near Hamminkeln, a task which they completed without loss.

In May 1945, their aircraft helped to transport elements of the 1st Airborne Division to Norway and Denmark so that they could oversee the surrender of German forces in those countries. Although the War was now over, the reliance upon Transport Command for the delivery of supplies in fact grew, and over the coming months the Squadron was busily employed in the movement of freight and passengers to destinations all over Europe. 299 Squadron was disbanded on the 15th February 1946.

Commanders of 299 Squadron