List of Winners
| Season | Team | Title | |
|---|---|---|---|
| 2026 | ![]() | Raith Rovers | 4. |
| 2025 | ![]() | Livingston FC | 2. |
| 2024 | ![]() | Airdrieonians FC | 2. |
| 2023 | ![]() | Hamilton Academical | 3. |
| 2022 | ![]() | Raith Rovers | 3. |
| 2020 | ![]() | Inverness CT | 3. |
| 2020 | ![]() | Raith Rovers | 2. |
| 2019 | ![]() | Ross County FC | 3. |
| 2018 | ![]() | Inverness CT | 2. |
| 2017 | ![]() | Dundee United | 1. |
| 2016 | ![]() | Rangers FC | 1. |
| 2015 | ![]() | Livingston FC | 1. |
| 2014 | ![]() | Raith Rovers | 1. |
| 2013 | ![]() | Queen Of The South | 2. |
| 2012 | ![]() | Falkirk FC | 4. |
| 2011 | ![]() | Ross County FC | 2. |
| 2009 | ![]() | Dundee FC | 2. |
| 2008 | ![]() | Airdrieonians FC | 1. |
| 2007 | ![]() | St. Johnstone FC | 1. |
| 2006 | ![]() | Ross County FC | 1. |
| 2005 | ![]() | St. Mirren FC | 1. |
| 2004 | ![]() | Falkirk FC | 3. |
| 2003 | ![]() | Inverness CT | 1. |
| 2002 | ![]() | Queen Of The South | 1. |
| 2001 | ![]() | Airdrieonians FC (old) | 3. |
| 2000 | ![]() | Airdrieonians FC (old) | 2. |
| 1999 | ![]() | Alloa Athletic | 1. |
| 1997 | ![]() | Falkirk FC | 2. |
| 1996 | ![]() | Stranraer FC | 1. |
| 1995 | ![]() | Stenhousemuir FC | 1. |
| 1994 | ![]() | Airdrieonians FC (old) | 1. |
| 1993 | ![]() | Falkirk FC | 1. |
| 1992 | ![]() | Hamilton Academical | 2. |
| 1991 | ![]() | Hamilton Academical | 1. |
| 1990 | ![]() | Dundee FC | 1. |

















