Nikola Jakimovski

Born in Skopje (hometown Kriva Palanka), Jakimovski is a product of FK Makedonija Gjorče Petrov youth system. He joined their first team in the 2008–09 season, competing in the Macedonian First League. In 2010, he signed with Hungarian Ferencvárosi TC but after not having many chances he ended up loaned in the second half of the 2010–11 season to Macedonian top league FK Teteks. On 24 August 2011 he signed a contract with Serbian club FK Javor Ivanjica.

Ferencvárosi TC

Jakimovski only played one match on Ferencváros' side. He came in as a late substitute in a game against Győri ETO, that Ferencvárosi TC won by 3:0 .

Nagoya Grampus

On 12 December 2012 Nikola Jakimovski signed a contract with Japanese club Nagoya Grampus. He made his debut on in Nagoya Grampus' one all draw against Júbilo Iwata on 2 March 2013.

Jagodina

At the end of 2013 he returned to Europe, after a year with Nagoya Grampus, Jakimovski moved to Serbian SuperLiga side FK Jagodina on loan.

Italian Serie B

In January 2015 he signed a 6-months contract with Italian Serie B side Varese and got the shirt number 32. Following the team bankruptcy in summer 2015 he remain unattached till 3 September 2015, when he was free to sign with Como, becoming first Macedonian player to play for the team.

Nikola Jakimovski is eligible to represent North Macedonia and Bulgaria at international level. He represent Macedonia at under-17 and under-19 levels, and has been part of the Macedonian U-21 team from 2011 to 2012. On 1 October 2015 Bulgaria manager Ivaylo Petev prepare a call up for Jakimovski.