Popsugar Entertainment Award Season How Many Grammys Does Taylor Swift Have? Taylor Swift Won Her First Grammy When She Was Only 20, and That Was Just the Beginning 11 February 2019 by Kelsie Gibson View On One Page Photo 1 of 9 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 1 2008 Grammy nominations: 1 Best new artist How many she won: 0 Previous Next Start Slideshow Award SeasonGrammy AwardsTaylor SwiftMusic