In January 1938 he went to Spain.
In Spain, he flew I-15s in the 1^a Escuadrilla.

Following a period at the newly established Grupo de Transición y Eventualidades (pilot’s pool) at Celrá, sargento Álvaro Muñoz López was posted on 8 March to the I-15-equipped 1^a/26, the squadron being led by Osipenko.

Osipenko left Spain on 28 June 1938 and he was replaced as CO of the 1^a/26 by capitán Chindasvinto González García.
During his time in Spain he claimed at least 1 victory flying the I-15.
He had flown 80 operational sorties and taken part in 30 aerial combats in Spain.

On 22 February 1939, Osipenko was decorated with the Gold Star of the Hero of the Soviet Union and the Order of Lenin for his performances in Spain. By this time Osipenko already had left Spain.

On 11 May 1939, Anatoly Serov (a veteran from Spain) was killed, during a long-range training flight in UTI-4 trainer, together with the female pilot Mayor Paolina D. Osipenkova, who also was killed (Osipenkova was a women record holder and the wife of Osipenko).
They were both buried in Moscow’s Red Square, just outside the walls of Kremlin.

During the Second World War, he served in the 20 AD.

Mikhail Yakushin (another veteran from Spain) finished the war as commander of the 215 IAD. Included in this division was the 8 IAP under the command of Osipenko. The 215 IAD operated over East Prussia during 1944.

Osipenko ended the war with at least 1 biplane victory.

Claims:

Kill no.	Date	Time	Number	Type	Result	Plane type	Serial no.	Locality	Unit
	1938
1	??/??/38		1	Enemy aircraft	Destroyed	I-15		Spain	1a/26

Biplane victories: 1 destroyed.
TOTAL: 1 destroyed.

Sources:
Air Aces Home Page - Jan Safarik
Polikarpov I-15, I-16 and I-153 Aces - Mikhail Maslov, 2010 Osprey Publishing, Oxford, ISBN 978-1-84603-981-2
Spanish Republican Aces – Rafael A. Permuy López, 2012 Osprey Publishing, Oxford, ISBN 978-1-84908-668-4