An engineer by training, he was first elected prime minister in 1992, when he was 29, and served in the post until 1998, when the SDSM lost the election.
Inženjer po struci, Crvenkovski je prvi put za predsednika vlade izabran 1992, kada je imao 29 godina, a na njenom čelu bio je do 1998. godine kada je SDSM izgubila izbore.