From Prof. Oddfellow's sketchbook:

"Playing piano under difficulties."  From Popular Mechanics, 1911.

"Are ships supposed to sail above us?"  From 1942.

"Many think that Egypt is upside down [because the Nile flows from south to north]" (Marci Haines, Ancient Egypt).  And it's true.  Our photographic proof is courtesy of the San Diego Air & Space Museum Archives.

"Seascape with upside down view," scanned by the Wellcome Library, London.

"The statue of Agassiz, Stanford University after Earthquake April 18, 1906."

"Inverted photo of Mrs. Van Hoof."  Yet surely a photo is inverted only if we turn it upside down and then write a caption upon it.

From Beasts and Men by Jean de Boschère, 1918.

From Songs of Singularity or Lays for the Eccentric by the London Hermit, Walter Parke, 1875.

You've heard that Australia is upside down.  Even if the earth isn't a globe, Australia is still upside down, as proven by this flat earth map from 1893.  Here's a larger view of the map over at Wikimedia.

From Southern Illinois State Normal University's Obelisk yearbook, 1920.