I think the word “win” is off-putting in the context of RPGs, which we’ve always been told (or we’ve always told ourselves) are games you don’t play to win. It makes it sound like you’re playing to win, rather than playing for the experience of play, playing to spend time with friends, playing to find out what happens in a story, etc. I think that wariness is worth pushing back against, though: Just like you can play a board game with a clear win condition and have goals that supersede winning—an excuse to have fun with friends being a prominent frontrunner—I think we should be able to recognize that RPGs can and do allow for this too. If by “win” we just mean either “end the game when someone achieves a predetermined goal,” or, “play for a set period of time, number of turns, or number of sessions, and then assess who best met predetermined goals,” I feel like we do that quite a lot.
One of my favorite campaigns of all time, in fact, was a Cold Ruins of Lastlife game on Gauntlet Hangouts. That game is a soulslike variant of Dungeon World, including special advancement tracks for when your amnesiac PC either reclaims the lost knowledge of a dead world, or inspires hope for a bright new world. After you advance along one track or the other a certain number of times, the game text advises you that you should start wrapping up the game. The way we discussed it in play, though, was definitely in terms of “winning”—but maybe we were more comfortable with this because it was more like when you win a cooperative game than when you win a competitive game. (And the fact that it was inspired by a video game series that is very much about winning may have something to do with it, but I got the impression most players didn’t have much experience with that series.) When we achieved that final advancement, we took turns narrating an epilogue of how we changed the world.
I also think D&D more generally has moved toward a model of being “winnable” in later editions, especially the 4th edition that’s clearly inspired by World of Warcraft and tactical minis games. Every adventure/module that sees you facing (even if not fighting!) a “final boss” is one that can be won. I have loved plenty such scenarios.
I might even go so far as to say that RPGs do win/loss games better than board games. If you play a cooperative board game for hours and then lose at the end, while it doesn’t undo the fun you had along the way, it can feel pretty deflating. When you “lose” in an RPG, it can be just as exciting or affecting as when you win. The setting for Blades in the Dark and Ghost Lines started, after all, when John Harper’s players “lost” at Dungeon World. And in a similar situation, a failed skill challenge in D&D 4e led to a tragic but fascinating variant of the published setting we played, turning our “town hub” into a tent city surrounding a massive sinkhole to hell. At least it left us adventurers with plenty of work for future sessions.
Perhaps I’m being too loose with terminology, but I think if we can think charitably about what “winning” means, and not necessarily think of it as connected to social dominance (and all the toxic masculinity stuff that comes with it), we can probably think of a lot more examples of RPGs we’ve enjoyed winning at.