Ukraine said it damaged multiple defence air systems as well as radar stations and a control centre as it struck a Russian air base in Crimea.
Kyiv has increased its attacks on the annexed region in recent months, delivering a hammer blow to Moscow as it caused extensive damage to its Black Sea Fleet.
Ukrainian forces said the strike on an airfield near the city of Dzhankoy caused Russia the loss of prized S-400 Triumph air defence systems and the death of up to 30 soldiers.
Military intelligence claimed three radars and other surveillance systems, including an air defence command-and-control centre, were wiped out in the attack.
The S-400 Triumph was first developed in 1993 and is believed to engage aircraft, cruise missiles and UAVs. It has a range of 250km and can intercept ballistic missiles in a 60km radius.
READ MORE: Putin left reeling as Russian ship is obliterated in jaw-dropping moment