| 1989 | Dallas Cowboys | NFL | Owner/President/General Manager | 1 | 15 | 0 | .063 | 0 | 0 | | Owner serves as team's de facto General Manager |
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| 1990 | Dallas Cowboys | NFL | Owner/President/General Manager | 7 | 9 | 0 | .438 | 0 | 0 | | Owner serves as team's de facto General Manager |
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| 1991 | Dallas Cowboys | NFL | Owner/President/General Manager | 11 | 5 | 0 | .688 | 1 | 1 | Lost Div | Owner serves as team's de facto General Manager |
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| 1992 | Dallas Cowboys | NFL | Owner/President/General Manager | 13 | 3 | 0 | .813 | 3 | 0 | Won SB | Owner serves as team's de facto General Manager |
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| 1993 | Dallas Cowboys | NFL | Owner/President/General Manager | 12 | 4 | 0 | .750 | 3 | 0 | Won SB | Owner serves as team's de facto General Manager |
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| 1994 | Dallas Cowboys | NFL | Owner/President/General Manager | 12 | 4 | 0 | .750 | 1 | 1 | Lost Conf | Owner serves as team's de facto General Manager |
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| 1995 | Dallas Cowboys | NFL | Owner/President/General Manager | 12 | 4 | 0 | .750 | 3 | 0 | Won SB | Owner serves as team's de facto General Manager |
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| 1996 | Dallas Cowboys | NFL | Owner/President/General Manager | 10 | 6 | 0 | .625 | 1 | 1 | Lost Div | Owner serves as team's de facto General Manager |
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| 1997 | Dallas Cowboys | NFL | Owner/President/General Manager | 6 | 10 | 0 | .375 | 0 | 0 | | Owner serves as team's de facto General Manager |
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| 1998 | Dallas Cowboys | NFL | Owner/President/General Manager | 10 | 6 | 0 | .625 | 0 | 1 | Lost WC | Owner serves as team's de facto General Manager |
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| 1999 | Dallas Cowboys | NFL | Owner/President/General Manager | 8 | 8 | 0 | .500 | 0 | 1 | Lost WC | Owner serves as team's de facto General Manager |
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| 2000 | Dallas Cowboys | NFL | Owner/President/General Manager | 5 | 11 | 0 | .313 | 0 | 0 | | Owner serves as team's de facto General Manager |
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| 2001 | Dallas Cowboys | NFL | Owner/President/General Manager | 5 | 11 | 0 | .313 | 0 | 0 | | Owner serves as team's de facto General Manager |
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| 2002 | Dallas Cowboys | NFL | Owner/President/General Manager | 5 | 11 | 0 | .313 | 0 | 0 | | Owner serves as team's de facto General Manager |
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| 2003 | Dallas Cowboys | NFL | Owner/President/General Manager | 10 | 6 | 0 | .625 | 0 | 1 | Lost WC | Owner serves as team's de facto General Manager |
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| 2004 | Dallas Cowboys | NFL | Owner/President/General Manager | 6 | 10 | 0 | .375 | 0 | 0 | | Owner serves as team's de facto General Manager |
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| 2005 | Dallas Cowboys | NFL | Owner/President/General Manager | 9 | 7 | 0 | .563 | 0 | 0 | | Owner serves as team's de facto General Manager |
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| 2006 | Dallas Cowboys | NFL | Owner/President/General Manager | 9 | 7 | 0 | .563 | 0 | 1 | Lost WC | Owner serves as team's de facto General Manager |
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| 2007 | Dallas Cowboys | NFL | Owner/President/General Manager | 13 | 3 | 0 | .813 | 0 | 1 | Lost Div | Owner serves as team's de facto General Manager |
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| 2008 | Dallas Cowboys | NFL | Owner/President/General Manager | 9 | 7 | 0 | .563 | 0 | 0 | | Owner serves as team's de facto General Manager |
|---|
| 2009 | Dallas Cowboys | NFL | Owner/President/General Manager | 11 | 5 | 0 | .688 | 1 | 1 | Lost Div | Owner serves as team's de facto General Manager |
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| 2010 | Dallas Cowboys | NFL | Owner/President/General Manager | 6 | 10 | 0 | .375 | 0 | 0 | | Owner serves as team's de facto General Manager |
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| 2011 | Dallas Cowboys | NFL | Owner/President/General Manager | 8 | 8 | 0 | .500 | 0 | 0 | | Owner serves as team's de facto General Manager |
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| 2012 | Dallas Cowboys | NFL | Owner/President/General Manager | 8 | 8 | 0 | .500 | 0 | 0 | | Owner serves as team's de facto General Manager |
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| 2013 | Dallas Cowboys | NFL | Owner/President/General Manager | 8 | 8 | 0 | .500 | 0 | 0 | | Owner serves as team's de facto General Manager |
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| 2014 | Dallas Cowboys | NFL | Owner/President/General Manager | 12 | 4 | 0 | .750 | 1 | 1 | Lost Div | Owner serves as team's de facto General Manager |
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| 2015 | Dallas Cowboys | NFL | Owner/President/General Manager | 4 | 12 | 0 | .250 | 0 | 0 | | Owner serves as team's de facto General Manager |
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| 2016 | Dallas Cowboys | NFL | Owner/President/General Manager | 13 | 3 | 0 | .813 | 0 | 1 | Lost Div | Owner serves as team's de facto General Manager |
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| 2017 | Dallas Cowboys | NFL | Owner/President/General Manager | 9 | 7 | 0 | .563 | 0 | 0 | | Owner serves as team's de facto General Manager |
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| 2018 | Dallas Cowboys | NFL | Owner/President/General Manager | 10 | 6 | 0 | .625 | 1 | 1 | Lost Div | Owner serves as team's de facto General Manager |
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| 2019 | Dallas Cowboys | NFL | Owner/President/General Manager | 8 | 8 | 0 | .500 | 0 | 0 | | Owner serves as team's de facto General Manager |
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| 2020 | Dallas Cowboys | NFL | Owner/President/General Manager | 6 | 10 | 0 | .375 | 0 | 0 | | Owner serves as team's de facto General Manager |
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| 2021 | Dallas Cowboys | NFL | Owner/President/General Manager | 12 | 5 | 0 | .706 | 0 | 1 | Lost WC | Owner serves as team's de facto General Manager |
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| 2022 | Dallas Cowboys | NFL | Owner/President/General Manager | 12 | 5 | 0 | .706 | 1 | 1 | Lost Div | Owner serves as team's de facto General Manager |
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| 2023 | Dallas Cowboys | NFL | Owner/President/General Manager | 12 | 5 | 0 | .706 | 0 | 1 | Lost WC | Owner serves as team's de facto General Manager |
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| 2024 | Dallas Cowboys | NFL | Owner/President/General Manager | 7 | 10 | 0 | .412 | | | | Owner serves as team's de facto General Manager |
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| 2025 | Dallas Cowboys | NFL | Owner/President/General Manager | 3 | 5 | 1 | .389 | | | | Owner serves as team's de facto General Manager |
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