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The "Euromaidan" protests erupt in Ukrainian at the capital of Kyiv after the country-president at the time Viktor Yanukovych, shelves a free-trade deal with the EU in favor of closer ties to Russia
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Russian troops take over Ukraine's Crimean Peninsula and seize the regional parliament and government buildings.
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Protests were spreading across Ukraine and police fired live ammunition at demonstrators. The Ukrainian parliament voted to impeach Yanukovych and the interim government draws up an arrest warrant for the ousted president.
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The regional parliament holds a referendum on the status of Crimea just two weeks after the Russian military occupation begins. Over 95 percent vote in favor of joining the Russian Federation. Russia then signs a treaty with Crimean leaders to formally annex the peninsula.
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Pro-Russia separatist militants take control of the Donbas region of eastern Ukraine. These militants are believed to be supported by the Russian government, although Moscow has denied being directly involved in the conflict.
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Throughout the year, then-Canadian prime minister Stephen Harper announces numerous sanctions affecting Russian and Ukrainian companies and individuals involved in the annexation of Crimea and the armed separatist movement in Donbas.
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Canada sent around 200 Canadian Armed Forces (CAF) members every six months to help the Security Forces of Ukraine with military training. CAF members are expected to remain in the country until March 2022.
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Canada adds more Russian and Ukrainian individuals and companies to its sanctions list. So far, these measures have affected more than 440 individuals and entities.
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The Canada-Ukraine Free Trade Agreement is signed, entering into force in August of the following year.
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Actor and comedian Volodymyr Zelensky is elected President of Ukraine in a landslide vote, ushering in a new era of Ukraine-Russia relations.
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Whistleblowers allege that then-U.S. President Donald Trump had frozen US$400 million in security aid for Ukraine in an attempt to coerce Zelensky into investigating political rival Joe Biden and his family for damaging information.
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Satellite imagery shows a build-up of Russian troops on the border with Ukraine, stoking fears of a potential invasion. Zelensky also says that Russia had mobilized 100,000 soldiers in the border area, along with tanks and other heavy equipment
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Putin called for NATO to guarantee an end to eastward expansion while Biden threatened to impose harsh economic sanctions if Russia invades Ukraine.
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In a call with Zelensky, Biden promises that the U.S. and allies with the act "decisively" if Russia further invades Ukraine.
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Canada offers a $120-million loan to Ukraine aimed at bolstering the country's economy. Prime Minister Justin Trudeau says the federal government is also looking into expanding its UNIFIER mission, providing “defensive weapon and equipment" and imposing more sanctions on Russia.