| Year | Gm Season | Champion | GM/Manager | 1st Place Loser | GM/Manager |
|---|---|---|---|---|---|
| Pursue the Pennant Years | |||||
| 1990 | 1989 | San Diego Padres | Art Costa | Detroit Tigers | Jim Furtado |
| 1991 | 1990 | Pittsburgh Pirates | Mike Andrade | Detroit Tigers | Jim Furtado |
| 1992 | 1991 | SF Giants | Rick Borden | Pittsburgh Padres | Mike Andrade |
| 1993 | 1992 | Pittsburgh Pirates | Mike Andrade | St. Louis Cardinals | Jack Luddy |
| 1994 | 1993 | San Diego Padres | Art Costa | Chicago Cubs | Wayne Furtado |
| 1995 | 1994 | Oakland A's | Lee Robinson | Los Angeles Dodgers | Bob Ferreira |
| Strat-O-Matic Years | |||||
| 1996 | 1995 | Oakland A's | Lee Robinson | St. Louis Cardinals | Wayne Furtado |
| 1997 | 1996 | Chicago White Sox | Roger Rodrigues | Baltimore Orioles | Gary Santerre |
| 1998 | 1997 | Montreal Expos | Wayne Furtado | Milwaukee Brewers | Kevin Fernandes |
| 1999 | 1998 | San Diego Padres | Art Costa | Florida Marlins | Bob Schoonover |
| 2000 | 1999 | Baltimore Orioles | Gary Santerre | Texas Rangers | Jim Furtado |
| 2001 | 2000 | San Diego Padres | Art Costa | Baltimore Orioles | Gary Santerre |
| 2002 | 2001 | Baltimore Orioles | Gary Santerre | Detroit Tigers | Jim Furtado |
| Dynasty League Baseball Years (cards) | |||||
| 2003 | 2002 | SF Giants | Mike Bettencourt | Baltimore Orioles | Gary Santerre |
| 2004 | 2003 | San Diego Padres | Art Costa | Baltimore Orioles | Gary Santerre |
| 2005 | 2004 | Boston Red Sox | Paul Martinho | Baltimore Orioles | Gary Santerre |
| 2006 | 2005 | NY Yankees | Cory Santerre | Philadelphia Phillies | Wayne Furtado |
| 2007 | 2006 | Chicago Cubs | Jim Furtado | Baltimore Orioles | Gary Santerre |
| 2008 | 2007 | Detroit Tiger | Mike Bettencourt | San Francisco Giants | Wayne Furtado |
| 2009 | 2008 | San Diego Padres | Art Costa | New York Yankees | Cory Santerre |
| The Dark Times | |||||
| 2010 | 2009 | TBD | DNP | ||
| 2011 | 2010 | TBD | DNP | ||
| 2012 | 2011 | TBD | DNP | ||
| REBOOT - Dynasty League Baseball Online | |||||
| 2013 | 2012 | San Franciso Giants | JD Stoltzfus | Miami Marlins | Bob Schoonover |
| 2014 | 2013 | Boston Red Sox | Jim Furtado | Oakland A's | Igor Greenwald |
| 2015 | 2014 | Baltimore Orioles | Gary Santerre | San Francisco Giants | Joel Hinds |
| 2016 | 2015 | Milwaukee Brewers | Andy Paul | New York Yankees | Cory Santerre |
| 2017 | 2016 | Oakland A's | Tim Daluz | Milwaukee Brewers | Andy Paul |
| 2018 | 2017 | Baltimore Orioles | Gary Santerre | St. Louis Cardinals | Johnny Rocha |
| OOTP Years (The New Age) | |||||
| 2019 | 2019 | Los Angeles Dodgers | Bob Ferreira | San Diego Padres | Art Costa |
| 2020 | 2020 | Boston Red Sox | Jim Furtado | Seattle Mariners | Tim Daluz |
| 2021 | 2021 | Oakland Athletics | Glen Golden | New York Mets | Jeff LeRoux |
| 2022 | 2022 | San Francisco Giants | Tim Daluz | New York Yankees | Cory Santerre |