To have chocked, to have had made it close but never having made it all the way, to have continually come up short, to have lost in an often comical way. In reference to the Chicago Cubs of the MLB. Past tense of cub.
"Man the Cubs really cubbed it last year."
"The Cubs have cubbed it for 100 years now."
A sugar cubbie is a clean cut, good looking male under the age of 30, who has a healthy bank account that he uses to spoil his women. Sugar cubbies are often sought out by attractive women in their 30s, often referred to as pumas, not quite old enough to be a cougar, but a cougar in training.
She found herself the best of both worlds in dating that sugar cubbie. He always picks up the tab for dinner AND is still young enough to keep up with her in the sack.