No Contest - S1-E18
Revealing mistake: The photographs and news items relating to the Boston Barmaid Contest have been clumsily pasted onto a real newspaper. The paper upon which they were printed is cleaner and whiter than the off-white newsprint and the photographs have much greater contrast.
Answer: Here is the source of the "WE WIN" photo: http://www.oldnycphotos.com/nyny587ac.html Brooklyn, of all places.