TWO of Vladimir Putin's most crucial warplanes worth ￡290million have been shot down in the most recent blow to the despot's failing war in Ukraine.

       One of the Russian dictator's ￡260million spy planes disappeared and a vital bomber jet was set on fire after Ukrainian forces shot them out of the sky above the Azov Sea.

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       Putin's IL-22M command plane - one of two key aircraft hit on Sunday 4

       A ￡260m Russian A-50 spy plane (pictured) disappeared after the hit on Sunday Credit: EAST2WEST 4

       The Sunday attack came on the one-year anniversary of the Dnipro bombings in Ukraine which left over 45 dead Credit: AP

       They were blasted out of the air in one of Moscow's worst days for its air force since Russia's invasion in 2022.

       The IL-22M bomber, worth around ￡28million, just managed to make its way back to Anapa airport on fire after being hit, with a number of casualties.

       But the ￡260million A-50 spy plane disappeared soon after going on patrol near Zaporizhzhia at 9:10pm on Sunday.

       For now it is unclear if the aircraft were definitely hit by Ukrainian missiles possibly using a new NATO "miracle weapon" - or in a friendly fire ambush by the Russians.

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       After the IL-22M command plane was hit, air traffic control at Russian Anapa airport heard: "It's been hit, landing in Anapa.

       “Urgently need an ambulance and fire engine.”

       At least one senior Russian war commander was likely on board at the time.

       Russian Telegram channel Colonelcassad admitted there had been casualties on the aircraft.

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       Ukraine initially claimed to have downed the planes close to Putin's beloved ￡3million Crimean Bridge.

       But it was reported that the command plane was shot over Strilkove, Kherson, miles away from the key bridge.

       Reports say the planes have been flying the same routes for months.

       The spy plane, now missing, recently underwent a ￡3million modernisation and refit.

       It is a key Soviet-era aircraft which uses radar to detect missiles and enemy planes.

       Ukraine's RBK outlet reported Ukrainian Air Force General Mykola Oleshchuk as saying: "This is for Dnipro! Burn in hell, you inhumans! PS No details yet".

       The plane losses came late on Sunday - the first anniversary of the notorious Dnipro bombing which took the lives of 46 people and left over 80 people wounded.

       Ukrainians - like Russians - are keenly aware of anniversaries, suggesting the plane attacks could have been a revenge strike.

       But Russian pro-war sources appeared to admit that Putin’s own forces could have shot down the planes in yet another friendly fire humiliation.

       In December a Russian fighter jet was shot down by one of Putin's own missiles in a botched military strike.

       And a Russian pilot nearly died in another embarrassing near-miss just days earlier.

       "It is finally clear that the Russian IL-22 in the Sea of Azov area was hit by the Russian air defence that defended the Crimean Bridge," stated the VChK OGPU Telegram channel, which has links to the security services.

       “When the plane was hit, the bridge had an alarm, and traffic was blocked.

       “The pilot was able to land the plane, and at least two people were injured."

       Russian Telegram channel Military Informant also said: “The damaged IL-22 reached the airfield and landed, as evidenced by leaked intercepted conversations on an open frequency, but with the A-50, apparently, everything is much sadder.

       “If the loss of the aircraft is confirmed, it will be a huge setback for domestic aviation since there are only a few such AWACS aircraft in service and are constantly in short supply at the front.”

       The channel described the aircraft hits as “another dark day for the Russian air forces”.

       The loss of the AWACS plane was “approximately equal to [the demise of] an aircraft carrier”.

       The same channel discussed unnamed “miracle weapons” provided by NATO and Pro-Kremlin political analyst Sergey Markov also speculated on “use of a new type of weapon by the Armed Forces of Ukraine".

       Russian Telegram channel FlightBomber - with close military contacts - today appeared to admit the catastrophic blow.

       “Tragedy is always tragedy. Especially when it's on this scale,” said a post.

       “Who is to blame for the deaths of the pilots, we probably won't know."

       The channel called for the Russian Defence Ministry - which did not initially comment on the Air Force blow - to come clean about what happened.

       Russia has suffered repeated losses from friendly fire, indicating faulty weaponry as well as poor command and control.

       Pro-war military channel Rybar admitted the possibility of friendly fire.

       “Sadly there were enough similar cases during the past two years, and there is no sign of improvement,” reported the channel.

       Ukrainian channel Crimean Wind reported: “As we are informed, a Russian A-50 AWACS aircraft was shot down over the Sea of Azov near Berdyansk and an IL-22 was shot down.…

       “The IL-22, falling, pulled towards Kerch - that is why the bridge was closed.”

       The channel said that all ships in the vicinity of the Crimeans Bridge had their transponders turned off today.

       Initially, Ukrainian sources had claimed responsibility for the attack - despite the Sea of Azov being hard to reach.

       Senior politician Yuri Mysyagin said: “At about 21:00, Ukrainian units fired at two aircraft of the Russian Air Force, namely an A-50 AWACS aircraft and an IL-22, located over the Sea of Azov.

       “The A-50 was shot down, and the IL-22 was shot down, but was in the air and trying to get to the nearest airfield, but disappeared from the radar, after the descent began, in the Kerch area.”

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       Commanders have been careful not to use the intelligence-gathering planes too close to the active war zone.

       According to reports Russia had just nine of the A50 planes in service and 30 IL-22Ms.

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       A Russian IL-22 command and control spy plane Credit: EAST2WEST