"Walking Away a Winner" is a song written by Tom Shapiro and Bob DiPiero, and recorded by American country music artist Kathy Mattea.

It was released in March 1994 as the first single and title track from the album Walking Away a Winner.

The song reached #3 on the Billboard Hot Country Singles & Tracks chart.

[1] Directed by Steven Goldmann, the video starts off in a mobile trailer in the desert.

It shows Kathy confronting her lazy boyfriend (who is sitting watching TV, obviously not caring and staring into space).