Kajmakoski was born in the city of Struga, South Macedonia, on 17 October 1983. When he was just 7 years old, he moved to Vienna, Austria, together with his family. Daniel has two brothers, Dalibor and Filip. Daniel participated in many competitions. He was 17 years old when he participated in a show for the first time. He reached top 12. In 2009, was his first performance in Macedonia at Ohrid Fest with the song “Nezhna ko princeza” which was composed and written by himself. Daniel has also participated in the Bulgarian show “Pej S’men. After that he returned to Vienna, where he got a job but meanwhile he always worked around the music. In 2010, he was part of the “One-Worl-Projekt” of Thomas Raber, which was one of the Austrian candidates for the Eurovision Song Contest 2011, but the jury didn’t vote it for the final show. In 2011, he wrote a song for Karolina Goceva called “Ne se vrajkas” which become a huge hit in Macedonia and in the Balkans.

In 2013, he appeared in the auditions of the first series of X Factor Adria. He sang the song “Red” by Daniel Merriweather on his first audition and already impressed everyone. Later, he won the show on 23 March 2014. Daniels first single came the summer right after his victory. The song is called “Skopje-Beograd” and it’s a duet between Daniel and one of the X-Factor juries, Željko Joksimović, who represented Serbia during the Eurovision Song Contest 2012 with the song Nije Ljubav Stvar and became 3rd in Baku, Azerbaijan

On May 22, 2016 he won the third season of Tvoje lice zvuči poznato (Serbian version of Your Face Sounds Familiar). After a wide pallet of enjoyed performances as Rammstein, Gibonni, Karolina Gočeva, Prince, and many more, he claimed the victory as Måns Zelmerlöw.