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Apple was the first company to reach a $1 trillion market capitalization, achieving this milestone in August 2018.

Microsoft reached a valuation of $1 trillion on April 25, 2019.

You're right. On Dec. 27, 1999, Microsoft's market cap hit hit $614 billion.

I might have confused it with some "inflation adjusted market cap" I read somewhere.

That’s 1.175 trillion in today’s dollars according to https://www.usinflationcalculator.com/