Introduced in 1990–91 as the B&Q Centenary Cup, the Scottish Challenge Cup is a distinct Scottish cup competition for clubs below the Premiership and, in some seasons, invited teams. It is not a continuation of the B Division Supplementary Cup. The 2019–20 final was not played because of the COVID-19 pandemic; Inverness Caledonian Thistle and Raith Rovers were declared joint winners.
| Season | Scottish Challenge Cup winner | Runner-up | Trophy |
|---|---|---|---|
| 2025/26 | Raith Rovers FC | Inverness Caledonian Thistle FC Final: 4-1. |  |
| 2024/25 SPFL Trust Trophy | Livingston FC | Queen's Park FC Final: 5-0. |  |
| 2023/24 SPFL Trust Trophy | Airdrieonians | The New Saints Final: 2-1. | |
| 2022/23 SPFL Trust Trophy | Hamilton Academical FC | Raith Rovers FC Final: 1-0. | |
| 2021/22 SPFL Trust Trophy | Raith Rovers FC | Queen of the South FC Final: 3-1. | |
| 2020/21 Scottish Challenge Cup | Not held The competition was not held because of the COVID-19 pandemic. | ||
| 2019/20 Tunnock’s Caramel Wafer Challenge Cup | Inverness Caledonian Thistle FC Raith Rovers FC | Shared title The final was not played because of the COVID-19 pandemic; Inverness Caledonian Thistle and Raith Rovers were declared joint winners. | |
| 2018/19 IRN-BRU Cup | Ross County FC | Connah's Quay Nomads Final: 3-1. | |
| 2017/18 IRN-BRU Cup | Inverness Caledonian Thistle FC | Dumbarton FC Final: 1-0. | |
| 2016/17 IRN-BRU Cup | Dundee United FC | St Mirren FC Final: 2-1. | |
| 2015/16 Petrofac Training Cup | Rangers FC | Peterhead FC Final: 4-0. | |
| 2014/15 Petrofac Training Cup | Livingston FC | Alloa Athletic FC Final: 4-0. | |
| 2013/14 Ramsdens Cup | Raith Rovers FC | Rangers FC Final: 1-0 after extra time. | |
| 2012/13 Ramsdens Cup | Queen of the South FC | Partick Thistle FC Final: 1-1 after extra time; Queen of the South won 6-5 on penalties. | |
| 2011/12 Ramsdens Cup | Falkirk FC | Hamilton Academical FC Final: 1-0. | |
| 2010/11 ALBA Challenge Cup | Ross County FC | Queen of the South FC Final: 2-0. | |
| 2009/10 ALBA Challenge Cup | Dundee FC | Inverness Caledonian Thistle FC Final: 3-2. | |
| 2008/09 ALBA Challenge Cup | Airdrie United | Ross County FC Final: 2-2 after extra time; Airdrie United won 5-4 on penalties. | |
| 2007/08 Scottish Challenge Cup | St Johnstone FC | Dunfermline Athletic FC Final: 3-2. | |
| 2006/07 Scottish Challenge Cup | Ross County FC | Clyde FC Final: 1-1 after extra time; Ross County won 5-4 on penalties. | |
| 2005/06 Bell’s Cup | St Mirren FC | Hamilton Academical FC Final: 2-1. | |
| 2004/05 Bell’s Cup | Falkirk FC | Ross County FC Final: 2-1. | |
| 2003/04 Bell’s Cup | Inverness Caledonian Thistle FC | Airdrie United Final: 2-0. | |
| 2002/03 Bell’s Cup | Queen of the South FC | Brechin City Final: 2-0. | |
| 2001/02 Bell’s Challenge Cup | Airdrieonians | Alloa Athletic FC Final: 2-1. | |
| 2000/01 Bell’s Challenge Cup | Airdrieonians | Livingston FC Final: 2-2 after extra time; Airdrieonians won 3-2 on penalties. | |
| 1999/00 Bell’s Challenge Cup | Alloa Athletic FC | Inverness Caledonian Thistle FC Final: 4-4 after extra time; Alloa Athletic won 5-4 on penalties. | |
| 1998/99 Scottish Challenge Cup | Not held The competition was not held this season. | ||
| 1997/98 Scottish Challenge Cup | Falkirk FC | Queen of the South FC Final: 1-0. | |
| 1996/97 Scottish Challenge Cup | Stranraer FC | St Johnstone FC Final: 1-0. | |
| 1995/96 Scottish Challenge Cup | Stenhousemuir FC | Dundee United FC Final: 0-0 after extra time; Stenhousemuir won 5-4 on penalties. | |
| 1994/95 B&Q Cup | Airdrieonians | Dundee FC Final: 3-2 after extra time. | |
| 1993/94 B&Q Cup | Falkirk FC | St Mirren FC Final: 3-0. | |
| 1992/93 B&Q Cup | Hamilton Academical FC | Morton Final: 3-2. | |
| 1991/92 B&Q Cup | Hamilton Academical FC | Ayr United FC Final: 1-0. | |
| 1990/91 B&Q Centenary Cup | Dundee FC | Ayr United FC Final: 3-2 after extra time. | |
