Possible Clues:

• Second at the ring brings courage to last year's winner
• Courage (slang)
• Glass container or slang courage
• In the tree trunk the teetotaller will get a drink from it
• Fifth place
• Might the teetotaller hold his liquor in a tree-trunk?
• The teetotaller in the tree trunk may be full of liquor
• Decanter, e.g.
• What's in it may not be for one's that 21 down
• Repress, with "up"