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Stanley Baldwin/Ramsey McDonald
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For more on marking an answer as the "Best Answer", please visit our FAQ.Baldwin: 1924 and 1935
MacDonald: 1923, 1929, 1931
The answer is not as straightforward as it seems because there were a number of coalitions and hung parliaments at that time.
In December 1923 the general election resulted in the Conservative Party being the largest party, but without a majority; the minority Labour government under MacDonald was not formed until six weeks later in January 1924 when it became clear that the Conservative Party would not be able to form a government, but that the Labour Party would be supported by the Liberal Party. Hence MacDonald only "won" the 1923 election in the sense that it resulted in him becoming prime minister for nine months.
Baldwin won the October 1924 election with a clear majority afterr Macdonald's government fell.
Macdonald won the 1929 election and formed a minority government.
The economic crisis in August 1931 resulted in Macdonald proposing economic reforms which the rest of the Labour cabinet would not accept. Instead of resigning, Macdonald and a few of his "National Labour" colleagues left the Labour Party and formed a coalition government with Conservatives and National Liberals; this National Government won the October 1931 election with a large majority, although it was predominantly a Conservative one.
The National Government was re-elected in 1935 but by that time Baldwin had taken over as prime minister.
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