To be faced with a situation which is pointless, as a successful outcome is impossible. This is usually expressed in terms of a sporting contest in which one of two outcomes is foreseen, either a hiding or nothing. The 'to' in the phrase indicates alternative outcomes, as in terms like '6 to 1' or 'dollars to doughnuts'.

The phrase has two applications. One scenario would be that of a team which is expected to win easily but has the betting odds so strongly in their favour that no kudos or reward, i.e. 'nothing' would be gained from victory. The other is that of a weak contestant who is expected to be beaten, i.e. get 'a hiding'.

The phrase is known from the early 20th century and originated as horse racing parlance. The earliest record of it 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 two 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."