For many years No 14 was the sole flying squadron in Palestine, but it began life at Shoreham on 3 February 1915. Unlike many of its contemporaries it did not go to France but left for the Middle East in November 1915. It operated in a corps reconnaissance role supporting operations in Palestine, Arabia and the Western Desert and acquired some fighters in May 1917, but these were formed into No 111 Squadron that August. The squadron moved to Greece in October 1918 but by February 1919 it had returned to Britain where it disbanded on the 4th of that month.

Ironically it was No 111 Squadron that was re-numbered No 14 on 1 February 1920 at Ramlah in Palestine. It would remain in Palestine for the next 20 years operating in detachments at Amman and Ramlah equipped successively with Bristol Fighters, DH9As, Fairey IIIFs, Gordons and in March 1938, Wellesleys. The entry of Italy into the war saw the squadron move to Egypt, back to Palestine and then to the Sudan, where it carried out raids against Italian bases in Eritrea.

The squadron re-equipped with Blenheims in September 1940, which it took to Egypt before returning to Palestine. It later took part in operations in Iraq and then returned to the Western Desert and re-equipment with Marauders in August 1942. With Marauders the squadron carried out coastal patrols, mine-laying and maritime reconnaissance operations as well as bombing missions, moving to Algeria from March 1943.

However, the squadron flew its last mission on 21 September 1943, effectively disbanding. It reformed on 24 October 1944 as an anti-submarine unit at Chivenor equipped with Wellington XIVs, beginning operations in February 1945 and continuing until disbandment on 1 June 1945. However, the squadron reformed the same day at Banff in Scotland when No 143, equipped with Mosquitoes, was re-numbered No 14, remaining there until 31 March 1946. The next day a new No 14 appeared in Germany at Wahn, when No 128 was re-numbered. Again flying Mosquitoes, these were retained until 1951 with the arrival of Vampires and then Venoms in 1953. Its role changed to that of day fighter when Hunters were received in 1955 continuing in that capacity until disbandment on 17 December 1962.

Once again a new 14 Squadron arose, this time at Wildenrath from No 88 and was now flying Canberras in the Interdiction role. Another disbandment and re-formation occurred on 30 June 1970 when No 14 (Designate) Squadron took over the numberplate and No 14 became a Phantom FGR 2 ground attack unit at Bruggen in Germany. However, Phantoms were merely a stop-gap measure for this role and the squadron converted to the Jaguar on 9 April 1975, continuing to operate this type until 1 November 1985 when Tornadoes replaced the Jaguars. With the closure of RAF Bruggen, the last RAF air base in Germany, in 2001, the squadron re-located to the UK and is currently based at RAF Lossiemouth.