Born in Escondido, California, Kirovski, is the son of Macedonian immigrants, He joined Manchester United's youth team in 1992, becoming the first American to sign with the club. He led the reserve team in scoring in 1996, but was not able to break into the first team because of work permit regulations. After that season, he signed with Borussia Dortmund in the German Bundesliga. Kirovski spent the next four seasons in Germany. He played in Dortmund's 1996–97 UEFA Champions League campaign, becoming the first American to win the competition. He earned significant playing time during the 1998–99 season, when Borussia loaned him out to second division club Fortuna Köln. In 2000, Kirovski signed with Portuguese club Sporting CP After a season there, he went back to England, signing with Football League First Division club Crystal Palace. In 2002, Kirovski signed with Birmingham City, but after one and a half seasons, he signed with the Los Angeles Galaxy. In his first season in MLS, Kirovski scored eight goals. In 2005, the Galaxy traded him to the Colorado Rapids for a first round pick in the 2007 MLS SuperDraft. After spending the 2008 season with the San Jose Earthquakes, he rejoined the Galaxy in a November 2008 trade. Kirovski enjoyed a successful stint with the Galaxy, winning an MLS Cup in 2011 with the club. On January 23, 2012, Kirovski retired from soccer but remained on the coaching staff for the LA Galaxy as an assistant coach. A member of Bruce Arena's coaching staff, Kirovski helped the team repeat as MLS Cup champions in 2012. Kirovski was appointed by the LA Galaxy as the club's Technical Director on January 10, 2013. As Technical Director, Kirovski was instrumental in the creation of the club's USL affiliate LA Galaxy II which was established in January 2014. Kirovski served as the point man in the Galaxy's pursuit and eventual signing of Mexican forward Giovani dos Santos in August 2015. He also aided the Galaxy in their signing of Jelle Van Damme a year later. Kirovski served as the lead in the Romain Alessandrini as well as the addition of Mexican international Jonathan dos Santos. The Galaxy's Technical Director led the team's pursuit of Swedish soccer legend Zlatan Ibrahimovic, who joined the . . "My job is constant— like the stock market, I have to know value of how much people pay— Sweden, France. I know what he can make in MLS, China, Germany. I know that and I am up-to-date with the market. You have to know the world markets in terms of how much people earn and the values of certain players. "The key to what I do is my network, built up over my whole career. That’s the key part."
Kirovski joined Los Angeles Galaxy as assistant coach immediately upon his retirement in January 2012. In January 2013, the Galaxy appointed him as the club's technical director.
