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I'm not sure this kind of experiment would fly against today's Google, but it worked in 2004.

What does 'fly against' mean in this case?

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up vote 5 down vote accepted

Fly against isn’t functioning as a single phrase here.

To fly in this case just means to work, to be successful, with a slight connotation that the risk involves skirting the rules of some authority. Against is in the sense of running an experiment against some configuration of circumstances. So the example could be rephrased:

I’m not sure if running this experiment using today’s Google will work, but it did work in 2004.

Edit: The OED doesn’t document this figurative usage of fly, so it’s presumably not just colloquial but also fairly new. Urban Dictionary does; it’s currently their eighth-ranked definition for it, with a good example:

Don't even try that. It ain’t gonna fly.

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