| Session/Year | Song Title | Writer(s) **Bolded names represent the Grand Prize Winner for that year |
| Jan/Feb 2024 | Remind Me of Me | Brenda Cay, Mitch Collins |
| Mar/Apr 2024 | Love Washes Off | Michael R.J. Roth |
| Jan/Feb 2023 | The Woman in Black | Tracy Richardson |
| Mar/Apr 2023 | Christine | Lacy Green |
| May/Jun 2023 | The Neon in Her Eyes | Craig Hendricks |
| Jul/Aug 2023 | Painting Pickets | Christine Merritt, Gregory Becker, Michelle Creber |
| Sep/Oct 2023 | Wine Well Spent | Eryn Michel, Kimberly Shires |
| Nov/Dec 2023 | Who I’m From | Trent Fisher, Terri Jo Box, Russell Sutton |
| Jan/Feb 2022 | Blue September Morn | Rich Deans |
| Mar/Apr 2022 | Out Where The Wind Blows Free | Dan Edwards |
| May/Jun 2022 | Ain’t No Wrong Way | Rachel Gore, Thomm Jutz |
| Jul/Aug 2022 | These Two Hands | Jim Chalker |
| Sep/Oct 2022 | Even the House Misses You | Laura Lemons |
| Nov/Dec 2022 | Long Line of Cars | Mason Caviness, Emily Rose |
| Jan/Feb 2021 | Some Boys Grow Up To Be Soldiers | Brian Estes |
| Mar/Apr 2021 | Angels | Diane Smith |
| May/Jun 2021 | Remembered | Cameron Burleson |
| Jul/Aug 2021 | Anymore | Chelsea McWilliams, Tim Allard |
| Sep/Oct 2021 | Road That Coal Made Black | Ryan T. Miller |
| Nov/Dec 2021 | Don’t Waste the Rain | Chuck Thomas |
| Jan/Feb 2020 | Asking For A Friend | Ryan T. Miller |
| Mar/Apr 2020 | Aphrodite Wire and Wood | Joe Black |
| May/Jun 2020 | Echo | Matt Dunn |
| Jul/Aug 2020 | Love Was Just a Word | Shawn Byrne |
| Sep/Oct 2020 | This Long Life | Mark Miller |
| Nov/Dec 2020 | The Blindness Excuse | William Simons |
| Jan/Feb 2019 | Evangeline | Jeremy Dion |
| Mar/Apr 2019 | Mary Dyer | Todd Hearon |
| May/Jun 2019 | Changing (While Staying The Same) | Mike Guiney |
| Jul/Aug 2019 | Cradle Of The Moon | Lucy LeBlanc |
| Sep/Oct 2019 | Where The River Runs Clear | Scott D. Smith |
| Nov/Dec 2019 | Parallel Universes | Larry E. Black |
| Jan/Feb 2018 | Every Drink Tells A Story (For Merle) | Gary Hale |
| Mar/Apr 2018 | Be Good To Your Woman | Thurston Wilkes |
| Jul/Aug 2018 | Which Way Is Home? | Brett Gurzick |
| Sep/Oct 2018 | If I Were A Bottle | Samantha Elin |
| Nov/Dec 2018 | The Captain’s Son | Ryan T. Miller |
| Jan/Feb 2017 | Language Of The Broken-hearted | Mike Guiney |
| Mar/Apr 2017 | Come And Go Town | Don Owens |
| May/Jun 2017 | My Prayin’ Knees | Patrycya Hill |
| Jul/Aug 2017 | Highway Sky | Adrian Gronseth |
| Sep/Oct 2017 | If It Mattered | Jane Fallon |
| Nov/Dec 2017 | Old Habits | Eryn Michel |
| Jan/Feb 2016 | Outlaws | Lizzie Quinlan |
| Mar/Apr 2016 | War Stories | Kevin Dudley |
| May/Jun 2016 | Billy (Off The Line) | Mark Rostenko |
| Jul/Aug 2016 | Set In Her Ways | Rick Leather |
| Sep/Oct 2016 | Get-Away Car | Kerann Christopherson |
| Nov/Dec 2016 | You Make Sense | Jay Madera |
| Jan/Feb 2015 | Lost And Found | Kristen Sullivan |
| Mar/Apr 2015 | No Such Thing (As You And Me) | Owen Danoff |
| May/Jun 2015 | Marriage Ain’t The End of Being Lonely | Emily Scott Robinson |
| Jul/Aug 2015 | She Only Loves Me When She Lies | Heath Johnson |
| Sep/Oct 2015 | Running Out Of Texas | Greg Stielstra |
| Nov/Dec 2015 | Tomorrow’s Just A Promise | Mike Guiney |
| May/Jun 2014 | Lonely Pretty Things | Blair Bodine |
| Jul/Aug 2014 | Smoke | Matt Jordan |
| Sep/Oct 2014 | Reasons To Run | Brittany Hadley |
| Nov/Dec 2014 | Riptide | Dave DeWhitt |
