Twilight Struggle
"Twilight Struggle" was the highest-ranked game on BoardGameGeek from December 2010 to January 2016. As of August 2018, the board game occupies a fifth spot. Being released in 2005 it is the oldest board game in the overall top 10 ranking.
The Master of Game
The Master of Game is a medieval book on hunting written by Edward of Norwich, 2nd Duke of York, between 1406 and 1413, of which 27 manuscripts survive. It is considered to be the oldest English-language book on hunting. It was reprinted in 1904 with a translation into modern English, an essay on medieval hunting, and a foreword by then-American President and noted hunter Theodore Roosevelt.