For example, experienced chess players losing repeatedly to a complete beginner because they're used to playing against stronger and stronger opponents as they were gaining their experience.

Huh? AFAIK, chess players pretty much never lose to players rated 400 Elo less, and higher rated players are more consistent. This applies double for Go.

I think a weaker version of this statement ("repeatedly"->"more often than one naively might expect") might be true for poker.