The moment you publicly compare yourself to the dominant player in your field, you have lost.
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No, I don't think so. I think the moment the dominant player starts comparing itself to you, like the way Office ran ads comparing itself to Google Docs they have a problem.
If you're not the dominant player, you want to make sure you can back your claims up though, because if customers try it once and they find the claim to be wrong, they'll never try it again.
Well, Apple ran those annoying Mac vs PC ads. And while the ads themselves may or may not have worked well, Apple has not lost in the personal computer field. (Well, depending on how you define "lost" I guess. But I think they haven't lost by most definitions.)
Considering they've stopped running those ads since gaining a ton of traction in the PC industry over the past few years, I think those ads are probably supporting evidence of GP's claim (if anything), not a counter-example.
Edit: I went back and actually reread what GP said and realized I was wrong if interpreted literally, but I took it to mean something more like "you know you're currently losing when you compare yourself to the competition". But yeah, my bad, you're definitely right under the literal interpretation - Apple didn't lose and may actually win at the end.