| South Sask League Champions |
| U15AA | U18AA |
| 2024 | Pat Blues | 2024 | Capitals |
| 2023 | Aces | 2022 | Vics |
| 2021 | Not Awarded (COVID 19) | 2021 | Not awarded (COVID 19) |
| 2020 | Not awarded (COVID 19) | 2020 | Not awarded (COVID 19) |
| 2019 | Pat Blues | 2018 | Rangers |
| 2018 | Monarchs | 2015 | Capitals |
| | | 2014 | Capitals |
| | | | |
| Female U18AA | Female U18A |
| 2024 | Rebels | 2017 | Tigers |
| 2023 | Rebels | | |
| 2022 | Rebels | | |
| 2021 | Not awarded (COVID 19) | | |
| 2020 | Not awarded (COVID 19) | | |
| 2019 | Rebels | | |
| 2018 | Ravens | | |
| 2016 | Ravens | | |
| 2014 | Capitals | | |
| 2012 | Capitals | | |
| 2011 | Capitals | | |
| | | | |
| Female U15A | Female U13AA |
| 2023 | Rebels Black | 2024 | Rebels Black |
| | | | |
| Hockey Regina League Champions |
| U15AA - HRI Joined the SS league in 2006/07 season | U18AA - HRI joined the SS league in 2007/08 season |
| 2006 | Kings | 2007 | Lumsden |
| 2005 | Notre Dame | 2006 | Hawks |
| 2004 | Hawks | 2005 | Hawks |
| 2003 | Lumsden | 2004 | Hawks |
| 2002 | Hawks | 2003 | Rangers |
| 2001 | Flyers | 2002 | Hawks |
| 2000 | Moose Jaw | 2001 | Rangers |
| | | 2000 | Hawks |
| |
| U13AA- HRI joined the South division in 2022/23 season | | |
| 2022 | Tigers | | |
| 2021 | Not Awarded (COVID-19) | | |
| 2020 | Not Awarded (COVID-19) | | |
| 2019 | Prairie Storm | | |
| 2018 | Prairie Storm | | |
| 2017 | Tigers | | |
| 2016 | Royals | | |
| 2015 | Lumsden Lions | | |
| 2014 | Blues | | |
| 2013 | Prairie Storm | | |
| 2012 | Prairie Storm | | |
| 2011 | Sabres | | |
| 2010 | Capitals | | |
| 2009 | Milestone Flyers | | |
| 2008 | Hurricanes | | |
| 2007 | Prairie Storm | | |
| 2006 | Rangers | | |
| 2005 | Prairie Storm | | |
| 2004 | Sharks | | |
| 2003 | Kings | | |
| 2002 | Balgonie Stars | | |
| 2001 | Kings | | |
| 2000 | Hawks | | |
| 1999 | Kings | | |
| | | | |
| U18A | U18B |
| 2024 | Prairie Storm | 2024 | Prairie Storm Lightning |
| 2023 | Mustangs | 2023 | Mustangs |
| 2022 | Falcons | 2022 | Moose Jaw Warriors |
| 2021 | Not Awarded (COVID-19) | 2021 | Not Awarded (COVID-19) |
| 2020 | Not Awarded (COVID-19) | 2020 | Not Awarded (COVID-19) |
| 2019 | Blues | 2019 | Prairie Storm Lightning |
| 2018 | Notre Dame Argos | 2018 | Prairie Storm Thunder |
| 2017 | Cupar Canucks | 2017 | Prairie Storm |
| 2016 | Notre Dame Hounds | 2016 | Prairie Storm |
| 2015 | Notre Dame Argos | 2015 | Prairie Storm |
| 2014 | Avalanche | 2014 | Shamrocks |
| 2013 | Rockies | 2013 | Wild |
| 2012 | Rockies | 2012 | Wild |
| 2011 | Cupar Canucks | 2011 | Aeros |
| 2010 | Notre Dame Hounds | 2010 | Blackhawks |
| 2009 | Cupar Canucks | 2009 | Wild |
| 2008 | Prairie Storm | 2008 | Rockets |
| 2007 | Southey Marlins | 2007 | Lumsden Lions |
| 2006 | Hawks | 2006 | Blades |
| 2005 | Hawks | 2005 | Hawks |
| 2004 | Stars | 2004 | Stars |
| 2003 | Southey Marlins | 2003 | Flyers |
| 2002 | Flyers | | |
| 2001 | Thrashers | | |
| 2000 | Prairie Storm | | |
| | | | |
| Midget 15 | Non Body Checking |
| 2015 | Estevan Bruins | 2019 | Capitals |
| 2014 | Melville Millionaires | | |
| 2013 | Wild | | |
| 2012 | Estevan Bruins | | |
| 2011 | Notre Dame Hounds | | |
| 2010 | Notre Dame Hounds | | |
| 2009 | Avalanche | | |
| 2008 | Crush | | |
| | | | |
| U15A | U15B |
| 2024 | Lumsden Lions | 2024 | Hawks |
| 2023 | Tigers | 2023 | Buffalos |
| 2022 | Lumsden Lions | 2022 | Lumsden Lions |
| 2021 | Not Awarded (COVID-19) | 2021 | Not Awarded (COVID-19) |
| 2020 | Not Awarded (COVID-19) | 2020 | Not Awarded (COVID-19) |
| 2019 | Cougars | 2019 | Royals |
| 2018 | Prairie Storm | 2018 | Mustangs |
| 2017 | Prairie Storm | 2017 | Blues |
| 2016 | Lumsden Lions | 2016 | Lumsden Lions |
| 2015 | Stars | 2015 | Prairie Storm Thunder |
| 2014 | Moose Jaw Warriors | 2014 | Prairie Storm Lightning |
| 2013 | Stars | 2013 | Prairie Storm Lightning |
| 2012 | Estevan Bruins | 2012 | Capitals |
| 2011 | Prairie Storm | 2011 | Capitals |
| 2010 | Rockies | 2010 | Wild |
| 2009 | Aeros | 2009 | Golden Seals |
| 2008 | Lumsden Lions | 2008 | Southey Marlins |
| 2007 | Lumsden Lions | 2007 | Hawks |
| 2006 | Stars | 2006 | Kings |
| 2005 | Southey Marlins | 2005 | Flyers |
| 2004 | Rangers | 2004 | Flyers |
| 2003 | Kings | 2003 | Rangers |
| 2002 | Kings | 2002 | Notre Dame Hounds |
| 2001 | Notre Dame Hounds | 2001 | Notre Dame Hounds |
| 2000 | Lumsden Lions | 2000 | Stars |
| 1999 | Bethune | | |
| | | | |
| U15A - Consolation | U15B - Consolation |
| 2013 | Sabres | 2013 | Panthers |
| 2012 | Moose Jaw Warriors | 2011 | Rockies |
| 2011 | Indian Head Chiefs | 2010 | Scouts |
| | | 2009 | Capitals |
| | | 2008 | Wolf Pak |
| | | 2007 | Lumsden Lions |
| | | 2006 | Petes |
| | | 2005 | Stars |
| | | 2004 | Bullets |
| | | 2003 | Bullets |
| | | 2002 | Hawks |
| | | 2001 | Phantoms |
| | | 2000 | Raiders |
| | | | |
| | U13A |
| | | 2024 | Buffalos |
| | | 2023 | Prairie Storm Lightning |
| | | 2022 | Rebels |
| | | 2021 | Not Awarded (COVID-19) |
| | | 2020 | Not Awarded (COVID-19) |
| | | 2019 | Moose Jaw Warriors |
| | | 2018 | Moose Jaw Warriors |
| | | 2017 | Moose Jaw Warriors |
| | | 2016 | Prairie Storm Thunder |
| | | 2015 | Moose Jaw Warriors |
| | | 2014 | Cougars |
| | | 2013 | Prairie Storm Thunder |
| | | 2012 | Prairie Storm Thunder |
| | | 2011 | Southey Marlins |
| | | 2010 | Wild |
| | | 2009 | Southey Marlins |
| | | 2008 | Southey Marlins |
| | | 2007 | Prairie Storm |
| | | 2006 | Rangers |
| | | 2005 | Prairie Storm |
| | | 2004 | Flyers |
| | | 2003 | Kings |
| | | 2002 | Vipers |
| | | 2001 | Stars |
| | | 2000 | Moose Jaw Warriors |
| | | | |
| | | | |
| U13B | U13C |
| 2024 | Pense Bulldogs | 2024 | Lumsden Lions |
| 2023 | Hawks | 2023 | Rebels Red |
| 2022 | Pense Bulldogs | 2022 | Lumsden Lions |
| 2021 | Not Awarded (COVID-19) | 2021 | Not Awarded (COVID-19) |
| 2020 | Not Awarded (COVID-19) | 2020 | Not Awarded (COVID-19) |
| 2019 | Pense Bulldogs | 2019 | Lumsden Lions |
| 2018 | Pense Bulldogs | 2018 | Panthers Female |
| 2017 | Lumsden Lions | 2017 | Lumsden Lions |
| 2016 | Shamrocks | 2016 | Lumsden Lions |
| 2015 | Tigers | 2015 | Shamrocks |
| 2014 | Mustangs | 2014 | Buffalos |
| 2013 | Barons | 2013 | Sabres |
| 2012 | Cupar Canucks | 2012 | Sharks |
| 2011 | Wild | 2011 | Lumsden Lions |
| 2010 | Prairie Storm Lightning | 2010 | Rockies |
| 2009 | Sharks | 2009 | Jets |
| 2008 | Flyers | 2008 | Chill |
| 2007 | Hawks | 2007 | Stars |
| 2006 | Prairie Storm | 2006 | Petes |
| 2005 | Hawks | 2005 | Kings |
| 2004 | Stars | 2004 | Petes |
| 2003 | Stars | 2003 | Sharks |
| 2002 | Rangers | 2002 | Raiders |
| 2001 | Vipers | 2001 | Sharks |
| 2000 | Rangers | 2000 | Raiders |
| 1999 | Stars | 1999 | Flyers |
| | | | |
| U11A | |
| 2024 | Prairie Storm Lightning | | |
| 2023 | Lumsden Lions | | |
| 2022 | Moose Jaw Warriors | | |
| 2021 | Not Awarded (COVID-19) | | |
| 2020 | Not Awarded (COVID-19) | | |
| 2019 | Moose Jaw Warriors Red | | |
| 2018 | Mustangs | | |
| 2017 | Lumsden Lions | | |
| 2016 | Buffalos | | |
| 2015 | Prairie Storm Thunder | | |
| 2014 | Wild | | |
| 2013 | Capitals | | |
| 2012 | Capitals | | |
| 2011 | Avalanche | | |
| 2010 | Prairie Storm Thunder | | |
| 2009 | Kings | | |
| 2008 | Sharks | | |
| 2007 | Prairie Storm Thunder | | |
| 2006 | Prairie Storm | | |
| 2005 | Stars | | |
| 2004 | Prairie Storm | | |
| 2003 | Kings | | |
| 2002 | Balgonie | | |
| 2001 | Kings | | |
| 2000 | Rangers | | |
| | | | |
| U11B | U11B - Consolation |
| 2024 | Blues | 2024 | Tigers |
| 2023 | Prairie Storm Lightning | 2023 | Tigers |
| 2022 | Pense Bulldogs | 2022 | Royals |
| 2021 | Not Awarded (COVID-19) | 2021 | Not Awarded (COVID-19) |
| 2020 | Not Awarded (COVID-19 | 2020 | Not Awarded (COVID-19) |
| 2019 | Lumsden Lions | 2019 | Pense Bulldogs |
| 2018 | Lumsden Lions | 2018 | Bisons |
| 2017 | Buffalos | 2017 | Royals |
| 2016 | Lumsden Lions | 2016 | Colts |
| 2015 | Prairie Storm Cyclones | 2015 | Buffalos |
| 2014 | Prairie Storm Lightning | 2014 | Blackhawks |
| 2013 | Rouleau River Dogs | 2013 | Aeros |
| 2012 | Southey Marlins | 2012 | Aeros |
| 2011 | Prairie Storm Thunder | | |
| 2010 | Milestone Flyers | | |
| 2009 | Southey Marlins | | |
| 2008 | Hawks | | |
| 2007 | Flyers | | |
| 2006 | Lumsden Lions | | |
| 2005 | Sharks | | |
| 2004 | Rangers | | |
| 2003 | Kings | | |
| 2002 | Rangers | | |
| 2001 | Lumsden Lions | | |
| 2000 | Lumsden Lions | | |
| 1999 | Sharks | | |
| | | | |
| U11C | U11C - Consolation |
| 2024 | Prairie Storm Lightning | 2024 | Prairie Storm Ice |
| 2023 | Royals | 2023 | N/A |
| 2022 | Lumsden Lions | 2022 | N/A |
| 2021 | Not Awarded (COVID-19) | 2021 | Not Awarded (COVID-19) |
| 2020 | Not Awarded (COVID-19) | 2020 | Not Awarded (COVID-19) |
| 2019 | Prairie Storm Thunder | 2019 | Pense Bulldogs |
| 2018 | Lumsden Lions | 2018 | Bengals |
| 2017 | Prairie Storm Lightning | 2017 | Cougars |
| 2016 | Buffalos | 2016 | Blues (Female) |
| 2015 | Royals | 2015 | Bisons |
| 2014 | Prairie Storm Lightning | 2014 | Wild |
| 2013 | Prairie Storm Thunder | 2013 | Milestone Flyers |
| 2012 | Barons | 2012 | Falcons |
| 2011 | Falcons | 2011 | Wild |
| 2010 | Sabres | 2010 | Bears |
| 2009 | Lumsden Lions | 2009 | Kings |
| 2008 | Rangers | 2008 | Rangers |
| 2007 | Prairie Storm Lightning | 2007 | Stingers |
| 2006 | Lumsden Lions | 2006 | Rangers |
| 2005 | Flyers | 2005 | Rangers |
| 2004 | Prairie Storm | 2004 | Rangers |
| 2003 | Flyers | 2003 | Rangers |
| 2002 | Sharks | 2002 | Sharks |
| 2001 | Blades | 2001 | Raiders |
| 2000 | Kings | 2000 | Blades |
| 1999 | Sharks | 1999 | Petes |
| | | | |
| U11 Female | U13 Female |
| 2023 | Rebels White | 2015 | Estevan |
| 2022 | Rebels Red | 2014 | Rampage |
| 2021 | Not Awarded (COVID-19) | 2013 | Lumsden Lions |
| 2020 | Not Awarded (COVID-19) | 2012 | Flames |
| 2015 | Moose Jaw | 2011 | Capitals |
| 2014 | Chill | 2010 | Capitals |
| 2013 | Capitals | 2009 | Fort Qu'Appelle Foxes |
| 2012 | Ice | 2008 | Southey Marlins |
| 2011 | Prairie Storm | 2007 | Royals |
| 2010 | Fort Qu'Appelle Foxes | 2006 | Moose Jaw Ice Caps |
| 2009 | Fort Qu'Appelle Foxes | 2005 | Moose Jaw Warriors |
| 2008 | Royals | 2004 | Fort Qu'Appelle Foxes |
| 2007 | Fort Qu'Appelle Foxes | 2003 | Fort Qu'Appelle Foxes |
| 2006 | Southey | 2002 | Moose Jaw Warriors |
| 2005 | Royals | 2001 | Hawks |
| 2004 | Hawks | 2000 | Cougars |
| 2003 | Royals | | |
| | | | |
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