The Winters Express won two awards in the 2009 National Newspaper Association's Better Newspaper Contest.

In this year's competition, the Express won first place for "Best Serious Column", written by Debra LoGuercio (DeAngelo) on April 17, 2008. The topic of the column was the April 7 raid on the Fundamentalist Church of Jesus Christ of Latter-Day Saints compound in Eldorado, Texas.

The Express also won third place for "Best Local News Coverage" for issues dated March 6 and September 25, 2008.