| You Win Again | |
| Cover: | MCC - You Win Again cover.png |
| Type: | single |
| Artist: | Mary Chapin Carpenter |
| Album: | Shooting Straight in the Dark |
| B-Side: | Moon and St. Christopher |
| Released: | October 1990 |
| Genre: | Country |
| Length: | 3:59 |
| Label: | Columbia |
| Prev Title: | Something of a Dreamer |
| Prev Year: | 1990 |
| Next Title: | Right Now |
| Next Year: | 1991 |
"You Win Again" is a song written and recorded by American country music singer Mary Chapin Carpenter. It was released in October 1990 as the first single from the album Shooting Straight in the Dark. The song reached number 16 on the Billboard Hot Country Singles & Tracks chart and number 6 on the RPM Country Tracks in Canada.[1]
The music video was directed by Bill Pope and premiered in early 1991.