| Unit Name: | No. 299 Squadron RAF |
| Dates: | 4 Nov 1943 – 15 Feb 1946 |
| Country: | United Kingdom |
| Branch: | Royal Air Force |
| Role: | Special Operations Transport |
| Command Structure: | No. 38 Group RAF |
| Identification Symbol: | No badge authorised |
| Identification Symbol Label: | Squadron Badge heraldry |
| Identification Symbol 2: | X9 (Jan 1944 – Feb 1946) 5G (Jan 1944 – Feb 1946) |
| Identification Symbol 2 Label: | Squadron Codes |
No. 299 Squadron was a Royal Air Force squadron during the Second World War and was part of No. 38 Group.
No. 299 Squadron was formed on 4 November 1943 form 'C' flight of 297 Squadron at RAF Stoney Cross, Hampshire as a special operations squadron. It became operational in April 1944 dropping SOE agents. During the Normandy landing the squadron first delivered paratroopers, and then returned to air-tow 16 Airspeed Horsa gliders across the English Channel. The squadron continued operations with resupply drops until 10 June when it returned to SOE duties.In between the SOE duties the squadron air-towed Horsa gliders for the Arnhem landing (Operation Market Garden), and the Rhine crossing (Operation Varsity). It was also involved in supply-dropping to resistance forces in Norway until the end of the war. On 7 October 1945, it lost five of its members in the crash of a Short Stirling IV in Rennes (Brittany).[1] At the end of the Second World War the squadron disbanded at RAF Shepherds Grove, Suffolk on 15 February 1946.
| November 1943 | January 1944 | Mks.I and II | ||
| January 1944 | February 1946 | Mk.IV | ||
| January 1945 | February 1946 | Short Stirling | Mk.V |
| 4 November 1943 | 15 March 1944 | RAF Stoney Cross, Hampshire | |
| 15 March 1944 | 9 October 1944 | RAF Keevil, Wiltshire | |
| 9 October 1944 | 25 January 1945 | RAF Wethersfield, Essex | |
| 25 January 1945 | 15 February 1946 | RAF Shepherds Grove, Suffolk |
| 4 November 1943 | 28 December 1943 | W/Cdr. R.W.G. Kitley | |
| 28 December 1943 | 19 September 1944 | W/Cdr. P.B.N. Davis, DSO | |
| 19 September 1944 | 1 November 1944 | W/Cdr. P.N. Jennings (acting after KIA of W/Cdr. Davis over Arnhem) | |
| 1 November 1944 | 31 December 1944 | W/Cdr. C.B.R. Colenso, DFC | |
| 31 December 1944 | September 1945 | W/Cdr. P.N. Jennings | |
| September 1945 | 15 February 1946 | W/Cdr. R.N. Stidolph |