In the Senate, not at all since 1976 - according to the MEDSL dataset found here. There have, however, been nine two-time matchups:- Jay Wolfe & Jay Rockefeller (WV; 2002 & 2008), Harvey Gant & Jesse Helms (NC; 1990 & 1996), Orin Hatch & Scott Howell (UT; 2000 & 2012), Paul Wellstone & Rudy Boschwitz (MN; 1990 & 1996), Joe Biden & Raymond Clatworthy (DE; 1996 & 2002), Jeanne Shaheen & John Sununu (NH; 2002 & 2008), Jack Reed & Robert Tingle (RI; 2002 & 2008), Cam Cavasso & Daniel Inouye (HI; 2004 & 2010), and Tom Strickland & Wayne Allard (CO; 1996 & 2002).
For House elections, this is much more common. There are a total of 108 pairs of candidates from the two main parties who have stood against each other at least three times in a general election since 1976. The record is held by Indiana's Pete Visclosky and Mark Leyva, who contested the state's 1st congressional district from 2002 to 2018. Leyva didn't run in 2012 or 2016, for a total of seven elections fought against each other. In this time period, Leyva's best performance was 38.6% of the vote in 2010; Visclosky won every election.
State |
District |
Candidates |
Matchups |
Duration |
Indiana |
1 |
Mark Leyva & Peter Visclosky |
7 |
2002 - 2018 |
South Carolina |
6 |
Gary Mcleod & James Clyburn |
6 |
1994 - 2006 |
California |
33 & 34 |
Lucille Roybal-Allard & Wayne Miller |
6 |
1998 - 2010 |
Missouri |
5 |
Emanuel Cleaver & Jacob Turk |
6 |
2006 - 2016 |
Massachusetts |
2 |
Edward Boland & Thomas Swank |
5 |
1976 - 1984 |
Ohio |
10 |
Clarence Miller & John Buchanan |
5 |
1982 - 1990 |
Oklahoma |
3 |
Frank Lucas & Frankie Robbins |
5 |
2008 - 2018 |
Oregon |
4 |
Art Robinson & Peter Defazio |
5 |
2010 - 2018 |
California |
27 & 30 |
Brad Sherman & Mark Reed |
5 |
2010 - 2020 |
Full results:
| State | District | Candidates | Matchups | Duration |
|----------------|----------|-------------------------------------------|----------|-------------|
| Indiana | 1 | Mark Leyva & Peter Visclosky | 7 | 2002 - 2018 |
| South Carolina | 6 | Gary Mcleod & James Clyburn | 6 | 1994 - 2006 |
| California | 33 & 34 | Lucille Roybal-Allard & Wayne Miller | 6 | 1998 - 2010 |
| Missouri | 5 | Emanuel Cleaver & Jacob Turk | 6 | 2006 - 2016 |
| Massachusetts | 2 | Edward Boland & Thomas Swank | 5 | 1976 - 1984 |
| Ohio | 10 | Clarence Miller & John Buchanan | 5 | 1982 - 1990 |
| Oklahoma | 3 | Frank Lucas & Frankie Robbins | 5 | 2008 - 2018 |
| Oregon | 4 | Art Robinson & Peter Defazio | 5 | 2010 - 2018 |
| California | 27 & 30 | Brad Sherman & Mark Reed | 5 | 2010 - 2020 |
| New York | 7 & 8 | Albert Lemishow & Benjamin Rosenthal | 4 | 1976 - 1982 |
| Indiana | 2 & 10 | Philip Sharp & Willian Frazier | 4 | 1976 - 1992 |
| California | 36 | George Jr & John Stark | 4 | 1980 - 1988 |
| Indiana | 9 | Floyd Coates & Lee Hamilton | 4 | 1982 - 1990 |
| Illinois | 9 | Herbert Sohn & Sidney Yates | 4 | 1984 - 1990 |
| North Carolina | 1 | Eva Clayton & Ted Tyler | 4 | 1992 - 1998 |
| California | 5 | Robert Dinsmore & Robert Matsui | 4 | 1992 - 1998 |
| Pennsylvania | 12 | Bill Choby & John Murtha | 4 | 1994 - 2002 |
| Maryland | 4 | Albert Wynn & John Kimble | 4 | 1996 - 2002 |
| Ohio | 2 | Charles Sanders & Rob Portman | 4 | 1998 - 2004 |
| Wisconsin | 1 | Jeffrey Thomas & Paul Ryan | 4 | 2000 - 2006 |
| Illinois | 1 | Bobby Rush & Raymond Wardingley | 4 | 2000 - 2010 |
| Louisiana | 5 | Lee Fletcher & Rodney Alexander | 4 | 2002 - 2002 |
| Washington | 6 | Doug Cloud & Norman Dicks | 4 | 2004 - 2010 |
| New Hampshire | 1 | Carol Shea-Porter & Frank Guinta | 4 | 2010 - 2016 |
| Tennessee | 9 | Charlotte Bergmann & Steve Cohen | 4 | 2010 - 2020 |
| Texas | 1 | Louie Gohmert & Shirley Mckellar | 4 | 2012 - 2018 |
| Louisiana | 1 | Lee Dugas & Steve Scalise | 4 | 2014 - 2020 |
| California | 2 | Dale Mensing & Jared Huffman | 4 | 2014 - 2020 |
| Massachusetts | 8 | Thomas Jr & William Barnstead | 3 | 1976 - 1980 |
| California | 6 | Phillip Burton & Tom Spinosa | 3 | 1976 - 1980 |
| Ohio | 8 | John Griffin & Thomas Kindness | 3 | 1976 - 1982 |
| Minnesota | 7 | Arlan Stangeland & Gene Wenstrom | 3 | 1978 - 1982 |
| Pennsylvania | 10 | Gene Basalyga & Joseph Mcdade | 3 | 1978 - 1984 |
| Ohio | 5 | Delbert Latta & James Sherck | 3 | 1980 - 1984 |
| Maryland | 2 | Clarence Long & Helen Bentley | 3 | 1980 - 1984 |
| New York | 23 & 28 | Frank Wicks & Samuel Stratton | 3 | 1980 - 1984 |
| Missouri | 7 | Gene Taylor & Ken Young | 3 | 1980 - 1986 |
| Michigan | 6 | Bob Carr & Jim Dunn | 3 | 1980 - 1986 |
| Utah | 1 | Gunn Mckay & James Hansen | 3 | 1980 - 1988 |
| Washington | 5 | John Sonneland & Thomas Foley | 3 | 1980 - 1992 |
| California | 37 & 40 | Donald Rusk & Jerry Lewis | 3 | 1980 - 1994 |
| Illinois | 21 | Melvin Price & Robert Gaffner | 3 | 1982 - 1986 |
| North Carolina | 11 | James Clarke & William Hendon | 3 | 1982 - 1986 |
| Connecticut | 1 | Barbara Kennelly & Herschel Klein | 3 | 1982 - 1986 |
| Oklahoma | 3 | Patrick Miller & Wes Watkins | 3 | 1982 - 1986 |
| Pennsylvania | 14 | John Clark & William Coyne | 3 | 1982 - 1994 |
| New York | 21 | Hamilton Jr & Lawrence Grunberger | 3 | 1984 - 1988 |
| California | 15 | Carol Harner & Tony Coelho | 3 | 1984 - 1988 |
| Minnesota | 7 | Arlan Stangeland & Collin Peterson | 3 | 1984 - 1990 |
| Ohio | 11 | Dennis Eckart & Margaret Mueller | 3 | 1986 - 1990 |
| North Carolina | 1 | Howard Moye & Walter Jones | 3 | 1986 - 1990 |
| California | 3 | Lowell Landowski & Robert Matsui | 3 | 1986 - 1990 |
| California | 28 | George Adams & Julian Dixon | 3 | 1986 - 1990 |
| California | 41 | Bill Lowery & Dan Kripke | 3 | 1986 - 1990 |
| Minnesota | 4 | Bruce Vento & Ian Maitland | 3 | 1988 - 1992 |
| Minnesota | 8 | James Oberstar & Jerry Shuster | 3 | 1988 - 1998 |
| Texas | 2 | Charles Wilson & Donna Peterson | 3 | 1990 - 1994 |
| North Carolina | 7 | Charlie Rose & Robert Anderson | 3 | 1990 - 1994 |
| Maryland | 7 | Kenneth Kondner & Kweisi Mfume | 3 | 1990 - 1994 |
| Michigan | 12 | John Pappageorge & Sander Levin | 3 | 1992 - 1996 |
| Pennsylvania | 3 | Charles Dougherty & Robert Borski | 3 | 1992 - 2000 |
| New York | 26 | Bob Moppert & Maurice Hinchey | 3 | 1992 - 2000 |
| Massachusetts | 6 | John Tierney & Peter Torkildsen | 3 | 1994 - 1998 |
| Wisconsin | 7 | David Obey & Scott West | 3 | 1994 - 1998 |
| Connecticut | 6 | Charlotte Koskoff & Nancy Johnson | 3 | 1994 - 1998 |
| Illinois | 17 | Lane Evans & Mark Baker | 3 | 1996 - 2000 |
| Pennsylvania | 11 | Paul Kanjorski & Stephen Urban | 3 | 1996 - 2000 |
| Maryland | 7 | Elijah Cummings & Kenneth Kondner | 3 | 1996 - 2000 |
| Washington | 6 | Bob Lawrence & Norman Dicks | 3 | 1998 - 2002 |
| Washington | 8 | Heidi Behrens-Benedict & Jennifer Dunn | 3 | 1998 - 2002 |
| Minnesota | 2 & 6 | Bill Luther & John Kline | 3 | 1998 - 2002 |
| Mississippi | 4 & 5 | Gene Taylor & Randy McDonnell | 3 | 1998 - 2006 |
| California | 47 & 48 | Christopher Cox & John Graham | 3 | 2000 - 2004 |
| Indiana | 5 | Dan Burton & Katherine Carr | 3 | 2002 - 2006 |
| Missouri | 4 | Ike Skelton & James Noland | 3 | 2002 - 2006 |
| Michigan | 1 | Bart Stupak & Don Hooper | 3 | 2002 - 2006 |
| Florida | 6 | Cliff Stearns & David Bruderly | 3 | 2002 - 2006 |
| California | 44 | Ken Calvert & Louis Vandenberg | 3 | 2002 - 2006 |
| Indiana | 9 | Baron Hill & Mike Sodrel | 3 | 2002 - 2008 |
| California | 40 | Christina Avalos & Edward Royce | 3 | 2002 - 2010 |
| New York | 16 | Ali Mohamed & Jose Serrano | 3 | 2004 - 2008 |
| Arizona | 4 | Don Karg & Ed Pastor | 3 | 2004 - 2008 |
| Florida | 14 | Connie Mack & Robert Neeld | 3 | 2004 - 2008 |
| Illinois | 15 | David Gill & Timothy Johnson | 3 | 2004 - 2010 |
| Pennsylvania | 16 | Joseph Pitts & Lois Herr | 3 | 2004 - 2010 |
| Nevada | 1 | Kenneth Wegner & Shelley Berkley | 3 | 2006 - 2010 |
| Indiana | 6 | Barry Welsh & Mike Pence | 3 | 2006 - 2010 |
| Arizona | 2 | John Thrasher & Trent Franks | 3 | 2006 - 2010 |
| Kentucky | 5 | Harold Rogers & Kenneth Stepp | 3 | 2006 - 2018 |
| New York | 7 & 12 | Allan Romaguera & Nydia Velazquez | 3 | 2006 -2016 |
| California | 17 & 20 | Jeff Taylor & Sam Farr | 3 | 2008 - 2012 |
| Texas | 15 | Eddie Zamora & Ruben Hinojosa | 3 | 2008 - 2014 |
| Iowa | 2 | David Loebsack & Mariannette Miller-Meeks | 3 | 2008 - 2014 |
| Kentucky | 1 | Charles Hatchett & Ed Whitfield | 3 | 2010 - 2014 |
| Wisconsin | 4 | Dan Sebring & Gwen Moore | 3 | 2010 - 2014 |
| California | 8 & 12 | John Dennis & Nancy Pelosi | 3 | 2010 - 2014 |
| Texas | 7 | James Cargas & John Culberson | 3 | 2012 - 2016 |
| Texas | 35 | Lloyd Doggett & Susan Narvaiz | 3 | 2012 - 2016 |
| California | 27 | Jack Orswell & Judy Chu | 3 | 2012 - 2016 |
| Ohio | 4 | Janet Garrett & Jim Jordan | 3 | 2014 - 2018 |
| Florida | 23 | Debbie Schultz & Joseph Kaufman | 3 | 2014 - 2018 |
| Wisconsin | 2 | Mark Pocan & Peter Theron | 3 | 2014 - 2020 |
| Washington | 9 | Adam Smith & Doug Basler | 3 | 2014 - 2020 |
| California | 9 | Antonio Amador & Jerry Mcnerney | 3 | 2014 - 2020 |
| Maryland | 4 | Anthony Brown & George Mcdermott | 3 | 2016 - 2020 |
| Michigan | 7 | Gretchen Driskell & Tim Walberg | 3 | 2016 - 2020 |
| Michigan | 12 | Debbie Dingell & Jeff Jones | 3 | 2016 - 2020 |
| California | 51 | Juan Jr & Juan Vargas | 3 | 2016 - 2020 |