Coach Pennington taught and coached in Van, Texas from 1984-1992 where he coached the varsity defensive backs and receivers. Also, from 1992-1999, he served as the offensive coordinator. During that time, the offense averaged 32 points per game.
In 2000, he and his family moved to Brenham, Texas; where he coached the wide receivers and helped with the cornerbacks on the defense. He returned back to Van where he served as the Head Football Coach and Athletic Director from 2002-2009. The Vandals were 62-26 including 4 district championships, 5 playoff appearances and a berth in the Class 3A state quarterfinals in 2008. In 2010 he moved again, this time, he coached quarterbacks at Porter High School. In 2011, coach proudly accepted the New Caney High School Head Football Coaching position.