| Battleground Park | Caitlin Cary | | | 3:16 | |
| Beauty Fades Away | Caitlin Cary | | 3 | 4:09 | |
| Big House | Caitlin Cary & Thad Cockrell | | 4 | 4:15 | |
| Big Town | Caitlin Cary | | | 3:45 | |
| By Eleven | Caitlin Cary | | | 4:05 | |
| Cello Girl | Caitlin Cary | | 2 | 4:40 | |
| Cello Girl | Caitlin Cary | | | 4:42 | |
| Cello Girl | Caitlin Cary | | | 4:41 | |
| Conversations About a Friend (Who's in Love With Katie) | Caitlin Cary & Thad Cockrell | | 3 | 7:24 | |
| Don't Make It Better | Caitlin Cary & Thad Cockrell | | 4 | 3:30 | |
| Empty Rooms | Caitlin Cary | | 4 | 4:19 | |
| Empty Rooms | Caitlin Cary | | | 4:19 | |
| Fireworks | Caitlin Cary | | 4 | 3:50 | |
| Fireworks | Caitlin Cary | | | 4:16 | |
| Hold on to Me | Caitlin Cary | | 3 | 4:08 | |
| I Ain't Found Nobody Yet | Caitlin Cary | | 4 | 5:07 | |
| I Don't Believe In Romance | Chris Stamey feat. Caitlin Cary | | | 4:49 | |
| I Want to Learn to Waltz With You | Caitlin Cary | | 3 | 6:18 | |
| I'm Staying Out | Caitlin Cary | | 3 | 3:53 | |
| In a While | Caitlin Cary | | 4 | 4:08 | |
| Keys to the Fair | Caitlin Cary feat. Chip Robinson | | 3 | 2:44 | |
| Let’s Go Downtown, Pt. 2 | Chris Stamey feat. Caitlin Cary & Chatham County Line | | | 4:19 | |
| Lorraine Today | Caitlin Cary | | 2 | 4:07 | |
| My Body Politic | Caitlin Cary & Shirlette Ammons | | | 2:23 | |
| Nursery Lie | Caitlin Cary | | | 4:06 | |
| Party Time | Caitlin Cary & Thad Cockrell | | 3 | 3:25 | |
| Party Time | Caitlin Cary & Thad Cockrell | | | 3:27 | |
| Please Break My Heart | Caitlin Cary & Thad Cockrell | | 4 | 4:11 | |
| Please Break My Heart | Caitlin Cary | | 4 | 3:18 | |
| Please Break My Heart | Caitlin Cary | | | 3:13 | |
| Please Break My Heart | Caitlin Cary | | | 3:18 | |
| Please Don't Hurry Your Heart | Caitlin Cary | | 3 | 5:09 | |
| Please Don't Hurry Your Heart | Caitlin Cary | | | 4:26 | |
| Please Take the Devil Out of Me | Caitlin Cary | | | 2:07 | |
| Pony | Caitlin Cary | | 4 | 3:49 | |
| Rosemary Moore | Caitlin Cary | | | 3:37 | |
| Rosemary Moore | Caitlin Cary | | | 3:38 | |
| Second Option | Caitlin Cary & Thad Cockrell | | 4 | 3:16 | |
| Second Option | Caitlin Cary & Thad Cockrell | | | 3:18 | |
| Second Option | Caitlin Cary & Thad Cockrell | | | ?:?? | |
| Shallow Heart, Shallow Water | Caitlin Cary | | 4 | 4:39 | |
| Sleepin' in on Sundays | Caitlin Cary | | 4 | 5:05 | |
| Some Tears | Caitlin Cary | | | 5:05 | |
| Something Less Than Something More | Caitlin Cary & Thad Cockrell | | 4 | 5:08 | |
| Sorry | Caitlin Cary | | 4 | 4:52 | |
| Sorry | Caitlin Cary | | | 4:28 | |
| Sorry | Caitlin Cary | | | 4:26 | |
| Stick to the Plan | The North Carolina Music Love Army feat. Caitlin Cary, Chip Robinson & Kenny Roby | | | 5:24 | |
| The Battle | Caitlin Cary & Ryan Adams | | | 3:00 | |
| The Battle | Caitlin Cary feat. Ryan Adams | | 4 | 3:01 | |
| The Battle | Ryan Adams W/ Caitlin Cary | | | 3:00 | |
| The Fair | Caitlin Cary | | 2 | 5:21 | |
| The Fair (band version) | Caitlin Cary | | 2 | 5:06 | |
| The Next One | Caitlin Cary | | 4 | 4:48 | |
| Thick Walls Down | Caitlin Cary | | 3 | 3:36 | |
| Thick Walls Down | Caitlin Cary | | | 3:22 | |
| Tonight I'll Be Staying Here With You (Jun 22, 2005, The Garage, Winston-Salem, NC) | Caitlin Cary & Thad Cockrell | | | ?:?? | |
| Too Many Keys | Caitlin Cary | | 3 | 3:49 | |
| Trickle of Whiskey | Caitlin Cary | | 3 | 3:05 | |
| Two Different Things | Caitlin Cary & Thad Cockrell | | 4 | 4:16 | |
| Waiting on June | Caitlin Cary & Thad Cockrell | | 4 | 4:37 | |
| Warm & Tender Love | Caitlin Cary & Thad Cockrell | | 4 | 4:45 | |
| What Will You Do? | Caitlin Cary | | 4 | 4:12 | |
| Whatever You Want | Caitlin Cary & Thad Cockrell | | 3 | 4:48 | |
| Withered & Died | Caitlin Cary | | | 4:30 | |
| You Don't Have to Hide | Caitlin Cary | | 4 | 3:33 | |
| Your Last Forever After | Chris Stamey feat. Caitlin Cary | | | 2:36 | |
