Might mean (unverified): Disappointed despite some small gain.
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We found one dictionary that defines the word look as if one had lost a shilling and found sixpence:

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  1. look as if one had lost a shilling and found sixpence: Wiktionary

Definitions from Wiktionary (look as if one had lost a shilling and found sixpence)

verb:  (idiomatic, UK) To look very disappointed.

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