Born into a noble Cossack family in Humań, Podolia, Polish–Lithuanian Commonwealth in 1646, Skoropadsky was educated in Kyiv-Mohyla Academy.

Ivan Skoropadsky was briefly an ambassador representing Cossack Hetmanate in negotiations with the Russian Tsar Peter the Great.

During the Great Northern War Skoropadsky was a Cossack colonel of the Ukrainian Starodub regiment and after Swedish army crossed into Ukraine in 1708, refused to join Ivan Mazepa who decided to switch sides and fight against Russia.

The fear of other reprisals and suspicion of Mazepa's newfound Swedish ally Charles XII prevented most of Ukraine's population from siding with the rebels.

Ivan Skoropadsky moved the capital of the Cossack Hetmanate from Baturyn which was razed by the Russian army for Mazepa's rebellion, to the town of Hlukhiv.