Rubuta ci gaba don wannan sakin layi - A matsayin voivode na Kiev, Chodkiewicz ya kare yankin daga mamayewar Tatar. A shekara ta 1558, ya sami nasara a Podolia a kan Khanate na Crimea. Wannan nasarar ta haɓaka darajar Chodkiewicz a matsayin kwamandan soja. A farkon Yakin Livonian, an daukaka shi zuwa castellan na Trakai da niyyar amfani da kwarewarsa a yaƙin. A cikin 1561, Grand Hetman Mikołaj "Black" Radziwiłł, Chodkiewicz, da ɗan'uwansa Hieronim sun jagoranci sojojin Lithuania zuwa Livonia inda suka sami nasara akan Tsardom na Rasha. Bayan wannan yaƙin, Chodkiewicz ya sami ci gaba zuwa filin Hetman na Lithuania. A ranar 20 ga Janairu 1564 Lithuanians a karkashin umurninsa sun kashe kwamandan Rasha Shuisky kuma sun kayar da sojojin Rasha a yakin Ula.
, wanda ya inganta matsayin Lithuania a cikin yaƙin. An yaba shi a matsayin gwarzo na yaƙi kuma an ɗaukaka shi zuwa castellan na Vilnius. Ƙaunar sarki ta ci gaba: Hrehory dan dan uwan Jan Hieronimowicz ya karbi matsayin mahaifinsa na marigayi a matsayin dattijo na Samogitia a 1564, ɗan'uwan Yurii, wanda ya tafi Moscow don tattaunawar diflomasiyya, ya zama castellan na Trakai kuma an nada Hrehory Babban Hetman na Lithuania a 1566. Ta haka ne, Hrehory Chodkiewicz ya zama mutum na biyu bayan Mikołaj "Red" Radziwiłł da Chodkiewiczs sun mallaki uku daga cikin manyan kujeru biyar a Majalisar Lords ta Lithuania. A shekara ta 1567, Chodkiewicz ya sake samun nasara a Livonia, a wannan karon a kan Masarautar Sweden.