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Electoral History
! Year ! ! Subject ! Party ! Votes ! % ! ! Opponent ! Party ! Votes ! % ! ! Opponent ! Party ! Votes ! % !
 * + Fairfax Board of Supervisors: Results 1995—2007
 * 1995
 * |Gerald Connolly
 * |Democratic
 * |4,478
 * |59
 * |Jeannemarie Devolites Davis
 * |Republican
 * |3,104
 * |40.9
 * 1995
 * |Gerald Connolly
 * |Democratic
 * |10,578
 * |55.8
 * |Jeannemarie Devolites Davis
 * |Republican
 * |8,371
 * |44.1
 * 1999
 * |Gerald Connolly
 * |Democratic
 * |14,309
 * |N/A
 * Unopposed
 * 2003
 * |Gerald Connolly
 * |Democratic
 * |98,419
 * |53.1
 * |Mychele B. Brickner
 * |Republican
 * |81,319
 * |43.9
 * Other
 * 5,465
 * 2.9
 * 2007
 * |Gerald Connolly
 * |Democratic
 * |113,830
 * |59.5
 * |Gary H. Baise
 * |Republican
 * |68,403
 * |35.8
 * |Gail Parker
 * |Independent Green
 * |8,990
 * |4.7
 * 2003
 * |Gerald Connolly
 * |Democratic
 * |98,419
 * |53.1
 * |Mychele B. Brickner
 * |Republican
 * |81,319
 * |43.9
 * Other
 * 5,465
 * 2.9
 * 2007
 * |Gerald Connolly
 * |Democratic
 * |113,830
 * |59.5
 * |Gary H. Baise
 * |Republican
 * |68,403
 * |35.8
 * |Gail Parker
 * |Independent Green
 * |8,990
 * |4.7
 * |59.5
 * |Gary H. Baise
 * |Republican
 * |68,403
 * |35.8
 * |Gail Parker
 * |Independent Green
 * |8,990
 * |4.7
 * |8,990
 * |4.7

Board of Supervisors
Connolly's career as a public official began on March 28, 1995 when he was elected Providence District Supervisor on the Fairfax County Board of Supervisors. He was reelected to a four-year term on the board in November of that same year. Connolly ran unopposed for re-election in November 1999. In 2003, he was elected Chairman of the Fairfax County Board of Supervisors and was reelected in 2007.

As Chairman of the ten-member board, Connolly balanced a budget of $4.5 billion and managed a county that, based on size, would make it the nation's thirteenth largest city, twelfth largest school district, and sixth largest office market. He served as Chairman of the County's Legislative Committee and Vice-Chair of the Economic Advisory Committee. Connolly also served as Chairman of the Board of the Northern Virginia Transportation Commission (NVTC), Chairman of the Northern Virginia Regional Commission (NVRC), and a member of the Board of the Metropolitan Washington Council of Governments (MWCOG), where he was chairman. He also chaired the region's Emergency Preparedness Taskforce and represented Fairfax County on the Board of the Virginia Association of Counties (VaCo), where he also served as president.

During his time on the Board of Supervisors, Connolly won multiple awards for leadership. In 2000, he received the MWCOG's Scull Award, the region's highest award for leadership, for his work on promoting telework throughout the Metropolitan Washington Region. Also in 2005, he was named Outstanding Local Elected Official of the Year by the Virginia Transit Association. In 2006, he was named Outstanding Local Official in the United States by the American Public Transit Association.