Ku qor sii wadida faqradan - Sidii voivode ee Kiev, Chodkiewicz wuxuu ka difaacay gobolka duulaankii Tatar. Sanadkii 1558, wuxuu guul ka gaaray Podolia oo ka dhan ah Crimean Khanate. Guushaan waxay sare u qaadday sumcadda Chodkiewicz oo ah taliyaha ciidanka. Markii uu bilowday Dagaalkii Livonian, waxaa loo dalacsiiyay inuu noqdo castellan of Trakai iyadoo ujeedkeedu yahay inuu xirfadiisa u adeegsado dagaalka. Sanadkii 1561, Grand Hetman Mikołaj "Madow" Radziwiłł, Chodkiewicz, iyo walaalkiis Hieronim waxay hogaamiyeen ciidankii Lithuania ee Livonia halkaas oo ay ku guuleysteen guusha ka dhanka ah Tsardom of Russia. Ololahan ka dib, Chodkiewicz waxaa loo dallacsiiyay inuu noqdo Hetman Field ee Lithuania. 20kii Janaayo 1564 kii Lithuania oo uu hogaaminayay ayaa dilay taliyaha Ruushka Shuisky waxayna ku adkaadeen ciidanka Ruushka Dagaalkii Ula
, taasoo si weyn u wanaajisay xaaladda Lithuania ee dagaalka. Waxaa loo aqoonsaday geesi dagaal waxaana loo dalacsiiyay xilka Castellan ee Vilnius. Raalli ahaanshaha boqortooyada ayaa sii socday: Hrehory wiil uu adeer u yahay Jan Hieronimowicz wuxuu helay booskii aabihii dhintay ee Odayga Samogitia sanadkii 1564, walaalkiis Yurii, oo u safray Moscow wadahadallo diblomaasiyadeed, wuxuu noqday castellan of Trakai iyo Hrehory waxaa loo magacaabay Grand Hetman of Lithuania sanadkii 1566. Sidaa darteed, Hrehory Chodkiewicz wuxuu noqday ninka labaad ka dib Mikołaj "Red" Radziwiłł iyo Chodkiewiczs waxay xakameynayeen saddex ka mid ah shanta kursi ee ugu sarreeya Golaha Lords ee Lithuania. Sanadkii 1567, Chodkiewicz wuxuu ku guuleystay guul kale Livonia, markan wuxuu ka soo horjeeday Boqortooyada Iswiidhan.