Vladimir Putin once left the Queen waiting for 14 minutes and during their tense meeting she made a pointed remark about the Russian leader which broke royal protocol.
Her Majesty is celebrating her Platinum Jubilee this weekend in London and regularly plays host to world leaders in the capital.
Back in 2003 she hosted the Russian President, who launched an invasion of neighbouring country Ukraine earlier this year, and they have long had a tense relationship.
In a 2014 D-Day memorial event in France, it was pointed out how the Kremlin leader stood close to the Queen but did not help her down the steps as US President Barack Obama stepped in to do so.
This came only months after Prince Charles was said to have compared Putin’s rule to the Nazi regime.
However, just over 10 years earlier the Queen and Russian president had a chilly encounter.
It was then Putin left her waiting, a tactic he has employed with other world leaders and in diplomatic events, but the Queen had a telling remark during the meeting.
According to David Blunkett, the then Home Secretary, his guide dog reacted defensively and barked at Putin during the 2003 event.
He apologised profusely to the Queen, but her telling remark may have been a rare moment she stretched royal protocols to comment on political matters.
Baron Blunkett told the BBC : "The only time I met Vladimir Putin was back in 2003 on an official visit and my then dog barked very loudly.
"I did apologise to the Queen who was obviously hosting. I don’t think I am giving anything away when I said, 'Sorry your Majesty about the dog barking.'
"She said, 'Dogs have interesting instincts, don’t they?'"
Only last year the Queen was asking other world leaders about the Russian president.
US president Joe Biden revealed the Queen asked him about Putin during the G7 summit in Cornwall, last year.
This was potentially the second time that Mr Biden broke royal protocol by revealing their conversations.
The president told reporters: "She wanted to know what the two leaders that I - the one I'm about to meet with, Mr Putin, and she wanted to know about Xi Jinping."
Since then, tensions between the UK and Russia, and opinions of Vladimir Putin will have only gotten worse in light of his bloody invasion of Ukraine.
On February 24, this year, Putin announced a “special operation” in Ukraine triggering an invasion of the country that is still ongoing.
In the intervening months, 10s of thousands have died on both sides, with reports suggesting Russia has suffered the heavier losses.
Millions of Ukrainians have fled their home country with countless having been internally displaced.
Speaking in his latest nightly address, Ukrainian President Volodymyr Zelensky said in the 98 days of fighting 446 children had been injured, 243 children killed and 139 have went missing.
He also claimed that Russia had kidnapped 200,000 Ukrainian children, including orphans and children torn from their family.
