1999 Allegheny County Executive election

The 1999 Allegheny County Executive election was held on November 2, 1999. The election was the first one following the 1998 passage of Allegheny County's charter, which replaced the existing County Commission with an elected County Executive and a fifteen-member County Council.

Both parties had contested primaries for the position. In the Democratic primary, County Coroner Cyril Wecht defeated County Commissioner Michael Dawida by a wide margin, winning the nomination with 57 percent of the vote. Businessman and civic activist Jim Roddey defeated County Commissioner Larry Dunn in a landslide, winning 68–32 percent. In the general election, Roddey narrowly defeated Wecht, 51–49 percent, becoming the first person to be elected County Executive, and, as of 2023, the only Republican to ever be elected to the position.