Kaliopi showed interest in music at a young age and in 1976, she entered in the Macedonian children's festival Zlatno Slavejče with the song Tebe Majka Ceka, previously sung by Tereza Kesovija.
Kaliopi later toured with the choir of Zapro Zaprov Razvigorče through Czechoslovakia, Slovenia (then within their native Yugoslavia) and Austria between 1978 and 1980.
She then joined the class of Marija Nikolovska, where she studied solo singing. She continued her training in the Music Academy in the class of Blagoja Nikolovski in 1984. She then joined a new band named after her and recorded their first two songs by request of the Macedonian Radio, titled Tomi and Nemoj Da Me Budis.
In 1986 the band Kaliopi participated in the Opatija festival and won 1st prize for the song Leo.
Many performances, festivals, show-programs for TV Zagreb, TV Belgrade, TV Sarajevo, TV Titovgrad followed, as well as a very large concert tour throughout all the major cities of the Soviet Union. In the time of her biggest popularity, Kaliopi and her former husban Romeo Gril, moved to Switzerland, which eventually led to the band breaking up. In 1987 Kaliopi took part in the Yugoslav pre-selection for the ESC with the song Emanuel which came 10th.
Kaliopi made a comeback in 1996 at SkopjeFest, Macedonia's pre-selection for the Eurovision Song Contest 1996, with the song Samo Ti. She was awarded first place by the jury and audience. The entry didn't receive enough points in the pre-qualifying round to reach the final.
After this Kaliopi decided to also write songs for other artists.
In 2002, Kaliopi submitted the song Pesna Za Tebe to Macedonian Television for the Macedonian pre-selection for the ESC 2002, eventually the song came 5th. In July, Kaliopi released a new singled called Najmila, which became an instant hit. In October, the album Najmila – Kaliopi Live and Unreleased was released.
In 2006 Kaliopi participated in the Macedonian national final for the ESC with the song Silna which came 6th. In 2009 she tried again to represent Macedonia but this time she came 2nd with the song Rum Dum Dum which was a duet with Naum Petreski.
Kaliopi released many succesful singles and albums and is stll a big star in her country and in other european countries as well.
In 2012 Kaliopi was internally chosen to represent Macedonia with the song Crno I Belo.