Not in this context it isn't, not necessarily. You've never heard an expression such as this: Who are the winners and losers with this? It isn't asking who deserves to win or who has earned a win, it's asking who benefits from whatever circumstance - whatever policy - whatever development - is being referred to. It isn't like asking who won the basketball game, it's asking who comes out ahead as a result of... whatever. A couple gets divorced, who are the winners and losers here? Often someone might say, neither the man nor the woman nor, especially, the children win. The winners are the attorneys, they benefit because people get divorced - even the nominally losing attorney might benefit, might win.
It's an expression, and not that uncommon a one I think.