Ivan Mikhailovich Obolensky
 | |
| Born | 1853 Moscow |
| Died | 28 February 1910 (aged 56–57) Saint Petersburg, Russian Empire |
| Allegiance | Russian Empire |
| Rank | Lieutenant-General |
| Battles/wars | Russo-Turkish War (1877–1878) |
Knyaz Ivan Mikhailovich Obolensky (Russian: Ива́н Миха́йлович Оболе́нский), or Prince John Obolenski (1853 – 28 February 1910), was an Imperial Russian Lieutenant-General.
He served as the Governor-General of Finland from 18 August 1904 to 18 November 1905. His predecessor Nikolai Ivanovich Bobrikov was assassinated in June 1904. He received a telegram from an unknown sender, saying: "We are expecting you in the near future -stop- The weather here is +200°C -stop- Bobrikov".
He was a member of a Rurikid princely family, whose ancestors once ruled one of the Upper Principalities. His mother was the Romanian-born aristocrat Olga Sturdza, daughter of Alexandru Sturdza (from a non-princely branch, 3rd cousin once removed of the Russian statesman Alexandru Sturdza), grand-treasurer of the Principality of Moldova, by Elena Ghika. His father was Knyaz (Prince) Mikhail Aleksandrovich Obolensky (1821–1886).
His term of office saw revolutionary turmoil in both Russia and the Grand Duchy of Finland. The Russian Revolution of 1905 resulted in a general strike in Finland and the replacement of the feudal Diet of Finland with the modern Parliament of Finland.
Knyaz Obolensky was murdered by revolutionaries in St. Petersburg at 28 February 1910.