Freakonomics looked into Microsoft's "Bing It On" challenge. From the blog post: "tests indicate that Microsoft selected suggested search words that it knew were more likely to produce Bing-preferring results. .... The upshot: Several of Microsoft’s claims are a little fishy.  Or to put the conclusion more formally, we think that Google has a colorable deceptive advertising claim."

I have to admit that I never bothered to debunk the Bing It On challenge, because the flaws (small sample size; bias in query selection; stripping out features of Google like geolocation, personalization, and Knowledge Graph; wording of the site; selective rematches) were pretty obvious.
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