Oleshky Raion (Ukrainian: Олешківський район) Formerly called Tsiurupynsk Raion, was one of the 18 administrative raions (a district) of Kherson Oblast in southern Ukraine. Its administrative center was located in the city of Oleshky. The raion was abolished on 18 July 2020 as part of the administrative reform of Ukraine, which reduced the number of raions of Kherson Oblast to five. The area of Oleshky Raion was merged into Kherson Raion. The last estimate of the raion population was 70,128 (2020 est.)

The Oleshky Raion was originally formed in 1923 in the Ukrainian SSR, in 1928 the Raion was renamed to the Tsiurupynsk Raion.

In May 2016, the Verkhovna Rada renamed Tsiurupynsk Raion back to Oleshky Raion conform with the law prohibiting names of the communist origin.

At the time of disestablishment, the raion consisted of four hromadas:

During the Russian occupation of Kherson Oblast, the Russian-installed governor Vladimir Saldo, signed a decree on July 8, 2022 and restorned the district with the name "Aleshkinsky District" and Ruslan Khomenko as its first governor.

At the time of reestablishment, the district is consisted of 9 departmennst.