Related Clues:

• Heartbreaking
• Only horse to defeat Man o' War
• 'A pity'
• Jets over Colts, 1969, e.g.
• Melancholic
• Unhappy
• Pretty pitiful
• In the dumps
• Improbable win
• In a blue state
• Deplorably bad
• Make unhappy
• Hangdog
• Truman's defeat of Dewey, e.g.
• Pensive, perhaps