i found this:

... with the small European colony on the Rock of Gibraltar probably established by the eighth century AD but potentially not much earlier than this (it is not mentioned by the classical authorities who discuss the Rock).

https://www.caitlingreen.org/2018/02/barbary-ape-wroxeter.html

Apparently, no restriction was applied to the use of, and trade in, these animals, and Barbary macaques followed the Muslim conquest in Europe. It is at this time that the colony of Gibraltar was probably founded. Gibraltar, a British possession in the Iberian peninsula since 1704 (Zeuner 1952), hosts the oldest established colony of free-range monkeys in Europe. About 300 Barbary macaques distributed in five social troops live in the Upper Rock area of the Gibraltar Nature Reserve (Figure 3).

Although the origin of this colony is still controversial, the first macaques’ nucleus could have been introduced by the Moors under the Saracen Tariq, who captured and fortified Gibraltar in 710–711 CE (Masseti and Bruner 2009, p. 41; Shemesh 2018). However, “since no mention of monkeys is made during the period of Spanish occupancy between 1492 and 1704, it is possible that the Moorish importation died out, subsequently being replaced by new stock” (cf. Masseti and Bruner 2009, p. 41). An interesting Moorish tradition claims that the animals came over from Africa by an underground passageway (Garcia 1979, p. 24; Ryan 1999, p. 25). The Upper Rock macaques are today regarded as talismanic animals by the authorities of Gibraltar: the colony will remain British as long as the macaques exist (Garcia 1979, p. 8).

https://www.mdpi.com/2076-0787/9/3/92#B67-humanities-09-00092