Heartache Medication debuted on the Billboard 200 at number 11, and number two on the Top Country Albums chart with 34,000 units, 23,000 of which are in pure album sales. On the Billboard 200, it left the top 100 on the week of November 2, 2019, spending eleven weeks on the chart. The album has sold 52,500 copies in the United States as of March 2020, and 161,000 units in total as of February 2020. In Canada, it debuted and peaked at number 18 on the Canadian Albums chart for the week of October 11.
