The computer software giant had hoped to overturn a £343m penalty for abusing its "dominant position" by effectively keeping rival software firms out of the market.
But Europe's second highest court threw out the appeal, saying it was "beyond dispute" that Microsoft obliged customers to buy its Windows operating system along with the company's Media Player software.
The Commission imposed the fine because it said Microsoft was using its powerful position in the computer software market to keep rivals out.
As well as the fine, Brussels insisted that Microsoft offer Windows without support software - and offer rival firms the necessary communications codes for their own software products to operate with Windows.
The European Court Of First Instance said the fact that Microsoft bundled Windows with its own software and did not charge any extra costs was "irrelevant".
The judges said tying the product together and not providing the necessary technical information to rivals to enter the same market was an abuse of Microsoft's dominant position.
The company is now studying the complex judgment.
It is almost certain to launch another appeal, this time to the European Court Of Justice, the final arbiter in anti-trust cases.
European Competition Commissioner Neelie Kroes said the verdict against Microsoft upheld a landmark Commission campaign to give consumers more choice in computer software markets.
He pointd out: "The decision sets an important precedent in terms of the obligations of dominant companies to allow competition, in particular in high tech industries.
"The ruling shows that the Commission was right to take its decision.
"Microsoft must now comply fully with its legal obligations to desist from engaging in anti-competitive conduct. The Commission will do its utmost to ensure that Microsoft complies swiftly."
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