"This Heartache Never Sleeps" is a song written by Tim Johnson and Daryl Burgess, and recorded by American country music artist Mark Chesnutt. It was released in April 1999 as the second single from the album I Don't Want to Miss a Thing. The song reached number 17 on the Billboard Hot Country Singles & Tracks chart and peaked at number 10 on the Canadian RPM Country Tracks chart.
"This Heartache Never Sleeps" debuted at number 75 on the U.S. Billboard Hot Country Singles & Tracks for the week of April 24, 1999.