As voivode of Kiev, Chodkiewicz defended the region from Tatar invasion. In 1558, he achieved a victory in Podolia against the Crimean Khanate. This victory raised prestige of Chodkiewicz as a military commander. On the onset of the Livonian War, he was promoted to castellan of Trakai with intention to use his skill in the war. In 1561, Grand Hetman Mikołaj "the Black" Radziwiłł, Chodkiewicz, and his brother Hieronim led the Lithuanian army into Livonia where they achieved victory against the Tsardom of Russia. After this campaign, Chodkiewicz was promoted to Field Hetman of Lithuania. On 20 January 1564 the Lithuanians under his command killed Russian commander Shuisky and defeated the Russian army in the Battle of Ula, which significantly improved Lithuania's standing in the war. He was hailed as war hero and promoted to castellan of Vilnius. Royal favor continued: Hrehory's nephew Jan Hieronimowicz received his late father's position as Elder of Samogitia in 1564, brother Yurii, who traveled to Moscow for diplomatic negotiations, became castellan of Trakai and Hrehory was appointed Grand Hetman of Lithuania in 1566. Thus, Hrehory Chodkiewicz became the second man after Mikołaj "the Red" Radziwiłł and the Chodkiewiczs controlled three out of five top seats in the Lithuanian Council of Lords. In 1567, Chodkiewicz achieved another victory in Livonia, this time against the Kingdom of Sweden.