Rosenberry played four years of college soccer at Georgetown University between 2012 and 2015, making 90 appearances and scoring four goals.

[2] While at college, Rosenberry also appeared for Premier Development League side Reading United AC in 2013 and 2015.

In the home opener, he was nominated for man of the match as well as being selected to the MLS Team of the Week.

Rosenberry scored his first goal for Colorado and added an assist against Toronto FC on September 15[12] He was named to the MLS Team of the Week in Week 23[13] In 2020, Rosenberry made 16 starts among 17 league appearances, and played a full 90 minutes in Colorado's MLS Cup Playoff first-round loss to Minnesota United FC.

[16] On January 5, 2017, following his first professional season, Rosenberry was called up to the senior United States squad by coach Bruce Arena.