After being an undisputed starter as General Caballero suffered relegation, Caballero signed a four-year contract with Olimpia on 7 February 2017, being immediately loaned to General Díaz.[2][3] On 15 June, he was recalled by his parent club.[4]
Sparingly used at Olimpia, Caballero rescinded his contract with the club on 10 November 2020, and announced that he would sign for a Brazilian club.[5] However, the move did not materialze,[6] and he spent the first half of the 2021 season without a club before signing for River Plate Asunción.[7]
On 28 December 2021, Caballero was announced at Libertad.[8]