Editorial Note: Usually transitive, especially in the form cupcake it. Thanks and credit go to Ben Zimmer for his research. Etymological Note: Ben Zimmer has suggested comparisons with other dessert-related terms, such as cakewalk, piece of cake, and pudding ‘an easy task,’ and easy as pie ‘very easy.’ However, there is also a noun cupcake ‘a homosexual man; an effeminate or ineffectual man,’ from an earlier (affectionate) term for a girl or woman, that could be related to the verb defined here.
Citations:
1991 Phil Jackman Baltimore Evening Sun (Md.) (July 24) “But I only used them two days” p. D2: In its last season before joining Big Ten hoops, Penn State is cup-caking it with UMBC, Morgan, Drexel, Miami (O), Buffalo, Lafayette, Cleveland State, Columbia, Toledo, etc. How would you like to be in charge of selling season tickets? 1999Usenet: nebr.sports.unl (Dec. 29) “[HUSKERS] Winging It, Vol. 19”: BYU, who cupcaked their way to a perfect season in ’84, gets it in the karma shorts again by getting whipped by unbeaten Marshall, one year after losing their bowl to unbeaten Tulane. 2001 Lee Yobbi @ Pojoaque Santa Fe New Mexican (Aug. 18) “Getting defensive” p. C1: Once teams start to double-team Duran on the line, you’ll get a glimpse—a fleeting glimpse—of Pojoaque’s two stand-out middle linebackers, Steve Garcia and Ruben “Cupcake” Sisneros. Don’t let the nickname fool you. This cupcake is not of the frosted variety. At 6-2, 205, he can stick a ball carrier. The nickname was just something that the seniors gave him during his freshman season as motivation. “They told me, ‘damnit, quit cup-caking it out there. Hit somebody!,’” Sisneros said. “And it just stuck from there.” 2002 [John] Buffalo Runners Forum (June 18) “Kyle Reid 5k”: I don’t care if Dan Grande cupcakes his way to victory; I’m just wishing that he would throw it down against the big dogs once in a while. 2005 Kevin Donahue Fanblogs.com (Aug. 11) “2005 Preseason USA Today Coaches Poll”: Auburn’s downfall last year was it’s puny schedule. If they hadn’t cupcaked it, they may have garnered the few extra votes that kept them out of the Orange Bowl. 2006 [OneOhioGirl] @ Medina, Ohio Ramblermania (Mar. 9) “Re: Syracuse”: Syracuse also plays a stronger regular season schedule than a lot of other schools so it’s not like they cupcake their way through the entire year. Yes, there is a BE bias to a degree but that isn’t Syracuse’s fault. 2006 Mike Fitzpatrick ABC News (U.S.) (Apr. 3) “Mets Get Break, Wagner Gets Save in Win”: Wagner, the All-Star closer who signed a $43 million, four-year contract with New York in the offseason to nail down tight games just like this one, worked the ninth for a save in his Mets debut. “Might as well get thrown right into the fire. No use cupcakin’ it,” Wagner said.