"From the Bottom of My Broken Heart" was performed for the first time on the ...Baby One More Time Tour in Pompano Beach, Florida, U.S.A at June 28, 1999. After its release as a single, Spears performed the song in a medley with "...Baby One More Time" at the 42nd Annual Grammy Awards. Spears was wearing a turtleneck and a full tulle skirt at the beginning of the performance, while dancers surrounded her with enormous hand fans. After singing a shortened version of the song, she then took a few moments to shuffle into a form-fitting red rhinestone outfit (with side cutouts) and emerged onto a stage to perform "...Baby One More Time." Jocelyn Vena of MTV included the performance on her list of Spears' Top 10 Best TV Performances. Spears also performed the song on her 2000s Crazy 2k Tour, where her dancers picked a boy from the audience and invited him onstage, while Spears dedicated the performance of "From the Bottom of My Broken Heart" to the boy. The same year, the song was performed for the last time on Oops!... I Did It Again Tour. Wearing glittery jeans and an orange halter top, she performed an acoustic version of the song with her guitarist Skip. Spears also performed "From the Bottom of My Broken Heart" and "Born to Make You Happy" on "Disney Channel in Concert" in 1999. The performances were recorded and included on Spears' first home video release, "Time Out with Britney Spears". The song was also performed in the television program "Good Morning America" on January 7, 2000 along with "...Baby One More Time".