How Many Grammys Did Taylor Swift Win 2024. By any metric, it's an incredible feat: Fearless and 1989, both of which have won two grammys.

4) 2024 grammy awards, taylor swift made history with her fourth album of the year win, taking the prize for midnights, as well as the pop vocal album award. Will taylor swift be the first singer to win album of the year four times?