Having graduated from the Faculty of Economics at the St. Clement of Ohrid University in Bitola in 1994 (where he dabbled in amateur theatre and boxing) he entered the nascent finance sector, and was the first person to trade on Skopje's stock exchange.

[16][17] Gruevski's paternal grandparents came from the Ottoman Macedonia village of Krušoradi, where his grandfather Nikolaos Grouios (Nikola Gruev) (1911–1940) was born.

Moreover, Gruevski also released a book in 2018 called "Experiences for the Future: Economic Effects of Different Types of International Capital Flows, With Particular Reference to the Republic of Macedonia"[25] The government under Ljubčo Georgievski sold the Macedonian Telecom to Hungarian Matáv and the OKTA oil refinery to Hellenic Petroleum.

[28] The coalition led by his party, VMRO-DPMNE, won the 1 June 2008 parliamentary election, their second electoral victory in a row, winning more than half of the seats in the parliament.

[30] The coalition led by his party, VMRO-DPMNE, won the 5 June 2011 parliamentary election, their third electoral victory in a row, winning 56 out of the 123 seats in the parliament.

Objections of misuse of state resources, including the blackmail of over one hundred thousand public servants to act as agitators were neglected, and the elections were declared valid.

In 2014, Gruevski began to rush plans through Parliament to create a tax-free autonomous trade zone that falls outside the purview of both domestic and international regulators.

'"[34] In 2015 the former prime minister and founder of the VMRO-DPMNE, Ljubčo Georgievski accused Gruevski's government it had a goal to serbianise the country, finally joining it to Serbia.

The demonstrations began following charges being brought against Zoran Zaev, the opposition leader, who responded by alleging that Gruevski had had 20,000 Macedonian officials and other figures wiretapped, and had covered up the murder of a young man by a police officer in 2011.

[36] In December 2017, Gruevski resigned as leader of the VMRO-DPMNE,[37] following the party's major defeat by the Social Democratic Union in local elections.

[38] In January 2017 the Macedonian Special Prosecutor's Office launched the 'Tank' investigation in which two individuals were accused of using their official position and authority in the period from February to October 2012 to complete an illegal public procurement of an armoured Mercedes-Benz car worth €600,000 and "fulfil the wishes" of Gruevski who was prime minister at the time.

[44] Gruevski was seen as having particularly close relations with the right-wing national conservative Fidesz's head, and Prime Minister of Hungary, Viktor Orbán, who opposed the Prespa agreement between Greece and Macedonia and supported VMRO-DPMNE's hardline position against it.

[48][49][50] Interpol alerted that Gruevski is wanted under an international arrest warrant and the Macedonian government filed a formal extradition request.

[48] Hungary's opposition parties are calling on the Hungarian government to arrest and quickly extradite the fugitive former prime minister back to Macedonia.

[8] Gruevski has condemned the Prespa agreement and stated that Prime Minister Zoran Zaev "scammed" and "tricked" the Macedonian people over the name change of the country and that Greek politicians imposed an unfavourable deal upon Macedonia that outlines exclusive claims over "antique history" by Greece.

[52] On 27 June 2019, Gruevski appeared handcuffed in a court in Budapest on a hearing closed for the public for his extradition requested by North Macedonia.

[57] On 19 March 2021, German politician Tobias Zech resigned from the Bundestag due to allegations that he received a large sum of money to campaign for former Macedonian PM Nikola Gruevski.