Play Mary-Kate and Ashley - Winners Circle Online

Game Overview

Mary-Kate and Ashley: Winners Circle is one of those Game Boy Color games that somehow makes brushing a pixelated horse feel weirdly satisfying. You play as the Olsen twins (pick your favorite, obviously) training for show jumping competitions—which means a mix of minigames for grooming, racing against the clock, and navigating obstacle courses that get surprisingly tricky by the third tournament.

The real charm is in the little details, like how your horse’s mane changes color based on which ridiculous accessory combo you pick, or the way Ashley’s victory animation has her doing this dorky little fist pump. It’s not exactly Red Dead Redemption, but the controls are snappy, and there’s something oddly compelling about shaving half a second off your best time just to unlock a new saddle with glitter trim.

If you played this as a kid, the nostalgia hits hard. If you didn’t? It’s still a weirdly fun time capsule of early 2000s girl-targeted games—where else can you match ribbons to your jodhpurs before attempting a triple jump? Just don’t blame me when you catch yourself humming the victory fanfare.