Crossword puzzle clue "first one to loser"

Canadian slang for loser that's also one letter away from "loser" and "poser"

First one to ___ (loser)

First rib-loser

Singer whose first hit was 1994's "Loser"

Loser in the first intercollegiate football game, 1869.

Loser in the first World Series, 1903

Loser to Apollo Creed in their first bout

First word across in the first-ever crossword (1913) and the first of a dozen appearances of the word in this puzzle's grid, written word search-style (left, right, down, and diagonally) ... Can you f