The present paper studies and publishes, for the first time, 14 military medals exhibited at the National Museum of Dāgistān Republic in Makhachkala, Caucasus. These medals are of great importance since they recorded historical events with different details. Moreover, they denoted awardees with their roles in public political life, as well as beliefs and religious doctrines. Moreover, they showed the insights of the military strife between the Russians and Mountain peoples and the role of Islamic Jihad leaders under the leadership of Imām Šāmil (Šumwīl) to liberate Caucasus from the Russian occupation. Šāmil awarded his military leaders these medals as a sort of motivation and appreciation for their prominent active role in the war against the Russians. These military medals played a vital role in expressing the geography and administrative divisions of Caucasus. Additionally, some medals referred to the Mountain territory as “The greatest Dāgistān" ()داغستان العظمي . The present paper tackles the religious significance of medals concerning expressing the nature of the Jihad situation in Caucasus in the 13th AH./19th AD. century, as in some Jihad expressions, such as moḥyī as-Sunnah (Sunnah rev-iver) wa Qāmi' al-Bid'ah (heresy suppressor); ( )محيي السنة وقامع البدعة - , Adām Taʿālā Dawlatuh (May his state live longer); ()أدام تعالي دولته . Medals played the interactive role in combining the records of historical resources and the biographies of the nobles through referring to the names of some Islamic Jihadist leaders in Dāgistān. They played a significant role in illustrating some recorded statements, including titles, names, dates, events, and some poetic lines. They were also important role in highlighting the artistic and decorative aspects. While some of them showed special insc-riptions of some weapons, spears and shields, others illustrated the signatures of many craftsmen following various Islamic artistic schools, confirming the super-ego of the Muslim craftsman.