Born in Podgorica, then part of SR Montenegro, SFR Yugoslavia, he begin his career in his hometown club FK Iskra Danilovgrad.
1999 he moved to FC Sutjeska Niksic which was a regular top flight side at that time. In summer 2004 he moved to their biggest Montenegrin rivals, FC Buducnost Podgorica, also playing back then in the First League of Serbia and Montenegro. In January 2005, during the winter break, he moved to France and joined League 2 side SCO Angers, where he played the rest of the season before returning to Buducnost in the following summer.
In summer 2006 the leagues of Serbia and Montenegro separated and Ivan Boskovic left Buducnost and moved to Serbia to play in the Super Liga, first with FC Vojvodina during the 2006–07 seasons, and next with FC Borac Cacak during the 2007–08 season.
In summer 2008 he returns to Montenegro and signs with a First League side OFK Grbalj where he will play during the following three seasons and become the league top-scorer in 2010 with 28 goals. In 2011, he moved to Uzbekistan and joined Nasaf Qarshi where he won 2011 AFC Cup and become top scorer of 2011 AFC Cup with 10 goals. Nickname is - "Boskogoal" and "Boshdagol".
In FC Grbalj, he became the top scorer of the Montenegrin Premier League in 2009 with 28 goals, and that record still stands.
He won 2011 AFC Cup and become top scorer of 2011 AFC Cup with 10 goals.
In Nakhon Ratchasima – Korat (Thailand) he played the most important role, being recognized as the league's top scorer and MVP in 2014.