Not exactly related, but looking at early-twentieth century presidential results in MD, one notes that in both 1904 and 1908 the GOP very narrowly won the popular vote in MD, yet most of the electoral votes went to Democrats. Wikipedia's explanation for this dichotomy is kind of confusing - can anyone explain why MD's electoral vote allocation was antimajoritarian? (Wikipedia mentions a "Wilson Rule" but doesn't coherently elaborate on it.)
At that time in Maryland, you voted for president by selecting individual electors, and one did not have to vote for a party slate (e.g. they could select 6 Democratic electors and 2 Republican electors). The electors were identified only by name, not by party. The Democrats had most of the well known statewide elected officials at the time, and several of them ran as electors.
The legislature appears to have done this intentionally to confuse voters who had less access to formal education. These presidential elections were also right around the time when they tried to impose an explicit literacy test but lost the referendum. 1904 was the first presidential election Maryland ran this way, and it continued through 1936.