The 19th IAP returned to the Leningrad Military District in October, and between 30 November 1939 and 13 March 1940 fought in the Winter War against Finland as part of the 54th Fighter Aviation Brigade of the VVS 7th Army of the Northwestern Front. It initially included three squadrons of I-16s and one I-15bis squadron; the latter was transferred to the north in mid-December and replaced by a new I-16-equipped 4th Aviation Squadron by the beginning of January. During the war, the regiment was officially credited with flying 3,646 sorties, downing three Finnish aircraft in aerial combat and destroying two on the ground, and 74 locomotives and 150 railcars destroyed in ground attacks; it suffered no losses. For its "exemplary performance of combat missions", the 19th IAP was awarded the Order of the Red Banner on 11 April.