Complex sentence: Since beginning at Navy, his teams have consistently earned more wins each consecutive season than the season preceeding it, including the school's first winning season, a 16-14 showing in the 2007-2008 season, in seven seasons.
Split into simpler sentences: Since beginning at Navy, his teams have consistently earned more wins each consecutive season than the season preceeding it. This streak includes the school's first winning season, a 16-14 showing in the 2007-2008 season, in seven seasons.