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The club was founded in 1990. They were promoted to the Macedonian First League in 2007 and were runners-up in the first two seasons. In 2010, the club finished ninth and lost a relegation play-off against Bregalnica Štip to relegate them to the Macedonian Second League, but due to financial problems Milano was relegated to the Macedonian Third League.
Season-by-season record
A season-by-season record of FK Milano Kumanovo league performances: