An Su-34 jet and a Mi-8 chopper were seen coming down near the Russian town of Klintsky within two hours of each other.
The town lies in the south-eastern region of Bryansk, about 25 miles from the Ukrainian border.
Another Mi-8 helicopter along with a Su-35 single seater fighter also came down, elsewhere in the Bryansk region.
Horror footage showed one of the the Mi-8 aircraft plummeting from the skies engulfed in flames as it slammed into the ground.
Then just two hours later, footage showed the Su-34 falling from the skies and its burnt wreckage on the ground.
The pilot and navigator in the plane failed to eject and were killed.
But Mash and Baza media outlets , which have with links to the authorities, said that the total number of downed aircraft was four – all returning from a combat mission.
There have been unconfirmed reports that the helicopter may have been shot down by friendly fire.
At first, the state news agency TASS reported one of the Mi-8s crashed due to “the engine catching on fire” citing preliminary information.
A source told TASS: “As of now, helicopter debris has been located.
“A fire started following the crash, it was extinguished quickly. The people who were abroad are dead.”
However, a video posted on the Russian pro-war Telegram channel, Voyenniy Osvedomitel, showed a helicopter high in the sky exploding, being thrown off course and then plunging earthwards in flames.
Kyiv has not made an official statement surrounding the incident.
Last year, Vladimir Putin was left humiliated when his troops shot down one of their own $34million fighter jets.