Most participial adjectives are made comparative and superlative with more and most. For example, we say more troubling and most sickening instead of troublinger and sickeningest. So, to many English-speakers, the superlative adjective winningest—meaning having the most wins—sounds wrong. And indeed some peevish grammarians hate the word. Yet despite the existence of grammatically unquestionable alternatives (most winning, best), winningest is deeply entrenched in sports commentary and is not going away any time soon. Those who dislike it might as well get used to it.
The Bryan brothers, the world’s winningest-ever professional doubles team, also play in a band that will perform Friday. [Los Angeles Times]
Clare Drake, the winningest coach in Canadian university hockey history, is a teacher of teachers. [Cult of Hockey blog at Edmonton Journal]
As for the top-five winningest quarterbacks in NFL history (by percent), four of the five are certified babes. [AV Club Twin Cities]
It comes as no surprise that Kiprusoff needs only a single dubya to become the franchise’s all-time winningest goalie. [Calgary Herald]