In 2007, the Cowboys again posted a 6–6 regular season record and a bowl win over the Indiana Hoosiers in the Insight Bowl. After their second straight bowl appearance, Gundy was rewarded with a contract extension through the 2013 season. Since 2008, Gundy has led the Cowboys to 59 wins, almost 10 wins per season on average. Many people would consider this to be the most successful period in Oklahoma State football history. He has also led the Pokes to twelve-straight bowl seasons, another Cowboy record.