Aside from figuring out what winning a contest means, when to use contests versus tests, crisis pools, Tales of Xadia’s challenges, etc., comes up quite a bit. There’s a lot of appeal to using contests, but inevitably, people run into applying them to a stereotypical RPG combat, with many PCs on one side and many baddies on the other. We’ll get into why you might not want to do that in more detail in a bit, but if you’re set on it, I’ll go over a few possibilities.
When You Really Love Hammers…
Most methods of involving more than two characters in a contest are going to hinge on who sets the difficulty for each roll.
More Than Two Characters on pg. 23 of the Cortex Prime Game Handbook is the most basic method to have multiple characters in a contest. Each character rolls. The one with the highest result sets the difficulty for all of the others to beat, and anybody who doesn’t do so takes a complication.
Another option is to have each character take turns being a “narrative lead”, framing the scene for that beat and rolling their pool to set the difficulty. This method is similar to Tales of Xadia’s challenges, with each player rolling to set the difficulty for referring everyone else, in addition to the GM doing it.
Or maybe each side’s characters contribute one die to their side’s pool, and then those pools are rolled against one another. The rolls would resolve everything that happens during each round. Hitches can stand in for consequences during the “round”, but you’d still have to figure out how to apply complications (or stress) at the very end.
Choosing the Right Tool
In the end, contests are intended to happen between two characters. Tales of Xadia sums it up nicely (emphasis mine):
In Tales of Xadia you may find yourself in conflict with a major Narrator character—a catalyst—over something important.
Contests are the moments the camera focuses on two personalities who have a beef with one another. Rather than cram every type of conflict in a game into the contest model, use different resolution methods depending on the situation or what would be more interesting/satisfying.
In many Cortex games, tests will be the workhorse for this. Unfortunately, tests are often overlooked for conflicts because many GMs assume you’re only going to roll a test when using a skill or avoiding a trap or something. If you think about it, you probably don’t want to get into a contest with the doorman at the club or some random extra. In those cases, just use a test. Quick roll-offs to keep the game moving—while still running the risk of a consequence—are what tests were made for.
As for how many different ways of resolving conflicts to use in a game, it’s tempting to throw the kitchen sink in with contests, action order, challenges, etc. For me, it’s better to choose two or three that focus on what the central conflicts of the game will be. For example, a game about vampire politics in a dimly-lit world might only need tests and contests. Meanwhile, personality clashes may not be important in a dungeon crawl (though they could be!), so it may only use tests and action order resolution.
You can even mix things up at the same time. Consider a large scene with many moving parts like the final battle in Avengers: Endgame. One or two PCs might be going toe-to-toe with Big Bads in contests, while others go round-by-round in action order with various minor GMCs and extras.
Trying to have contests do too much can create vagueness about what the boundaries of winning a contest are. contests are about preventing an opponent from doing something, can there instead be a related outcome? can winning a contest make other characters look at your character differently? One way to look at it is that winning a contest can give your narrative permission you didn’t have before to create assets or do other things. Another suggestion on the Cortex Discord was to have winning the contest result in creating an asset instead of inflicting a complication. I prefer having the asset already exist and winning means gaining narrative control over it, but either method works fine.
In the end, it’s about using the best method to give the experience that you want—and there’s nothing wrong with having more than one option. Just follow the fiction, and what seems like it will make for an exciting game.