| Year | Won | Margin | Democratic | Republican | Total |
|---|---|---|---|---|---|
| 2024 | R | 696 | 3,884 | 4,613 | |
| 2020 | R | 823 | 3,847 | 4,739 | |
| 2016 | R | 865 | 3,671 | 4,668 | |
| 2012 | R | 1,419 | 2,886 | 4,421 | |
| 2008 | R | 1,811 | 2,652 | 4,591 | |
| 2004 | R | 1,823 | 2,769 | 4,673 | |
| 2000 | R | 1,568 | 2,521 | 4,233 | |
| 1996 | D | 1,795 | 1,502 | 3,841 | |
| 1992 | D | 2,258 | 1,402 | 4,236 | |
| 1988 | D | 2,042 | 1,717 | 3,766 | |
| 1984 | D | 2,026 | 1,979 | 4,005 | |
| 1980 | D | 2,326 | 1,523 | 3,898 | |
| 1976 | D | 2,564 | 1,122 | 3,712 | |
| 1972 | R | 1,352 | 2,118 | 3,470 | |
| 1968 | D | 1,726 | 1,213 | 3,564 | |
| 1964 | D | 2,908 | 992 | 3,900 | |
| 1960 | R | 1,934 | 1,974 | 3,908 | |
| 1956 | D | 2,472 | 1,436 | 3,908 | |
| 1952 | D | 2,926 | 1,804 | 4,744 | |
| 1948 | D | 3,133 | 1,214 | 4,357 | |
| 1944 | D | 2,734 | 1,573 | 4,314 | |
| 1940 | D | 3,593 | 1,826 | 5,434 | |
| 1936 | D | 3,504 | 1,461 | 4,970 | |
| 1932 | D | 3,599 | 786 | 4,423 | |
| 1928 | D | 1,884 | 1,662 | 3,550 | |
| 1924 | D | 2,231 | 896 | 3,487 | |
| 1920 | D | 1,961 | 1,319 | 3,333 | |
| 1916 | D | 1,799 | 660 | 2,546 | |
| 1912 | D | 1,688 | 486 | 2,682 | |
| 1908 | D | 1,550 | 729 | 2,405 | |
| 1904 | D | 1,215 | 693 | 2,055 | |
| 1900 | D | 1,768 | 652 | 2,468 | |
| 1896 | D | 1,783 | 576 | 2,365 | |
| 1892 | D | 1,118 | 318 | 1,619 | |
| 1888 | — | — | — | — | |
| 1884 | — | — | — | — | |
| 1880 | — | — | — | — | |
| 1876 | — | — | — | — |
Oregon County sits in Missouri's remote Ozark Highlands, where low population density and a predominantly white, working-class demographic have produced some of the state's most lopsided Republican margins for over a decade.
The unraveling was not abrupt. The Democratic margin in Oregon County peaked at sixty-four points in 1932; it narrowed steadily over the late twentieth century. The 2000 election delivered the county to the Republican party for the first time in many years, by a margin of twenty-three points. By 2024, the margin had widened further.
The economic and demographic context is severe. Oregon County's median household income of $43,069 is among the lowest of any county in the United States; 24% of residents live below the federal poverty line. The county's voting pattern over the last decade is most similar to that of Indiana County and Gilmer County.