What’s the origin of the phrase ‘On a hiding to nothing’?
The phrase is known from the early 20th century and originated as horse racing parlance. The earliest record that I can find is from Arthur Binstead’s novel Mop Fair, 1905, or, to give it its glorious technicolor name, Mop Fair. Some Elegant Extracts from the Private Correspondence of Lady Viola Drumcree, the Fatherless Daughter of Feodorovna, Countess of Chertsey:
“They will, like the man who was on a hiding to nothing the first time Tom Sayers saw him, ‘take it lying down’.”
Two citations that demonstrate the alternative possible scenarios given above come from The Times and The Sunday Times, from the 1970s:
1975 - The Sunday Times: “The Indian batsmen were on a hiding to nothing. They could not win.”
1977 - The Times: “Derby know they are on a hiding to nothing at Fourth Division Colchester, who have a reputation as giant-killers.”
See also - Catch 22.