| Year | Won | Margin | Democratic | Republican | Total |
|---|---|---|---|---|---|
| 2024 | R | 3,392 | 4,922 | 8,384 | |
| 2020 | R | 4,040 | 5,112 | 9,236 | |
| 2016 | R | 3,850 | 4,910 | 8,881 | |
| 2012 | R | 4,607 | 5,168 | 9,829 | |
| 2008 | R | 4,653 | 5,497 | 10,221 | |
| 2004 | R | 3,978 | 5,386 | 9,415 | |
| 2000 | R | 3,672 | 4,645 | 8,368 | |
| 1996 | R | 3,488 | 3,498 | 7,438 | |
| 1992 | R | 3,953 | 4,311 | 8,968 | |
| 1988 | R | 3,851 | 5,317 | 9,229 | |
| 1984 | R | 3,543 | 5,192 | 8,746 | |
| 1980 | D | 4,416 | 3,998 | 8,545 | |
| 1976 | D | 3,956 | 3,659 | 7,792 | |
| 1972 | R | 1,354 | 5,155 | 6,555 | |
| 1968 | D | 911 | 508 | 6,054 | |
| 1964 | R | 237 | 3,922 | 4,159 | |
| 1960 | D | 1,056 | 405 | 2,966 | |
| 1956 | D | 2,132 | 361 | 2,705 | |
| 1952 | D | 2,559 | 771 | 3,330 | |
| 1948 | D | 240 | 33 | 2,105 | |
| 1944 | D | 1,822 | 51 | 1,873 | |
| 1940 | D | 1,979 | 26 | 2,005 | |
| 1936 | D | 2,418 | 21 | 2,440 | |
| 1932 | D | 1,720 | 12 | 1,736 | |
| 1928 | D | 1,620 | 97 | 1,717 | |
| 1924 | D | 1,344 | 53 | 1,397 | |
| 1920 | D | 932 | 113 | 1,062 | |
| 1916 | D | 1,152 | 47 | 1,226 | |
| 1912 | D | 743 | 9 | 822 | |
| 1908 | — | — | — | — | |
| 1904 | — | — | — | — | |
| 1900 | D | 597 | 42 | 679 | |
| 1896 | D | 793 | 32 | 838 | |
| 1892 | D | 357 | 4 | 597 | |
| 1888 | — | — | — | — | |
| 1884 | — | — | — | — | |
| 1880 | — | — | — | — | |
| 1876 | — | — | — | — |
Winston County sits in east-central Mississippi's piney-woods belt, where a declining manufacturing base and a population that has shrunk roughly 15% since 2000 have reshaped the electorate even as presidential margins continue to widen on the Republican side.
The shift began with civil rights. 1984 marked the realignment in Winston County, by a nineteen points margin. The Republican margin reached its widest at eighty-nine points in 1964. The 2024 margin was eighteen points.
The political shift has tracked, in Winston County, the political shift of the South more broadly. A 50% non-Hispanic-white share, a median household income of $53,031, and a 27% poverty rate describe the demographic context. The county's voting pattern over the last decade is most similar to that of Leake County and Grenada County.
