To go back to the start.

Phrase is believed to originated from early radio commentaries of football (or soccer if you prefer) matches by the BBC. The first live radio commentary featured a Division One match between Arsenal and Sheffield United, broadcast on 22nd January 1927. A grid of a football pitch divided into 8 numbered squares had been printed in the previous weeks Radio Times to enable listeners to know what square the ball was in, as inexpertly rendered below:-


      -----------------------------
      |      |      |      |      |
      |  8   |   6  |   4  |   2  |
      |      |      |      |      |
      -----------------------------
      |      |      |      |      |
      |  7   |   5  |   3  |   1  |
      |      |      |      |      |
      -----------------------------

The game being restarted from the goalkeeper's possession would be called back to square one. However as is clear from the diagram, only 1 in every 4 times would the ball actually 'be' in square one when the game was restarted by the goalkeeper. 'Back to square one' rolls off the tongue easier then alternatives such as back to square two or square seven, but the fact that the use of squares in football commentaries is a distant memory suggests that the squares gimmick did not enhance the action for the listener.

An alternative suggestion for the source of the phrase is from children's games such as hopscotch and snakes and ladders.

http://news.bbc.co.uk/sport1/hi/football/1760579.stm

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