Barnet and Orient first met back in 1965 at Underhill, when the Bees were a Southern League side. The competition was the London Challenge Cup 1st round and the visitors won 4-3 with Barnet goals coming from Tony Harding and two from Reg Finch. In 1971, the two clubs met at the same stage in the same competition and Orient, as they were back then, again ran out winners at Underhill; this time winning 2-1 with Barnet’s goal coming from Colin Powell.
By the time the two clubs next met, Barnet were in the 4th division of the Football League and the two sides met in the 2nd round of the Autoglass Trophy, a fore runner of the JPT, Leyton Orient, the East London club having reverted to their old name agin, won 1-0 again at Underhill.
In 1993/94, the clubs net three times. Two goals from Tony Lynch were not enough to prevent Orient winning the London Challenge Cup Final 3-2. Barnet having won promotion to the third tier of the Football League (then called Division 2), met Orient for the first time for league points. Orient won 4-2 at Brisbane Road; Dave Barnett and Kelly Haag scoring for the Bees and in the return at Underhill, Barnet beat Orient for the first time, winning 3-1 with goals from Mark Newson, Tony Lynch and Terry Gibson.
Despite the Bees being relegated at the end of that season, the two clubs still met the following season; in the 1st round of the Coca Cola (League) Cup, Barnet going through 5-2 on aggregate over two legs. Two goals apiece for Dougie Freedman and Mark Cooper gave Barnet a 4-1 win at Underhill and a 1-1 at Brisbane Road, Freedman scoring again, saw the Bees through to the 2nd round.
By the following season, 1995/96, Orient had joined the Bees in Division 3. Barnet won the league meeting at Underhill 3-0 with two goals from Lee Hodges and one for Alex Dyer while the return fixture ended in a 3-3 draw with Hodges on target again for the Bees and Sean Devine grabbing a brace.
In 1996/97, the match at Underhill was goalless but Barnet won for the first time at Brisbane Road with Linvoy Primus scoring the only game of the game. However, the following season, Orient completed a league double over Barnet, winning 2-0 at home and 2-1 at Underhill, Warren Goodhind scoring for Barnet.
In 1998/99, Barnet won 3-2 at Underhill with goals from mike Basham, Ken Charlery and Paul Wilson and drew 2-2 at Brisbane Road with goals from Stevie Searle and John Doolan. The home victory was the last time that Barnet have won against Orient. In 1999/00 both matches ended in draws; a goalless draw at Leyton and 2-2 at Underhill with goals from Paul Wilson and Mark Arber. Orient completed a league double for a second time in 2000/01; winning 3-1 at home, Omar Riza scoring for Barnet and 2-1 at Underhill, with Barnet slipping towards relegation. Darren Currie scored the Barnet goal.
In 2005, Barnet returned to league football after winning the Conference and resumed matches against Orient. Despite two Giuliano Grazioli goals, Orient won 3-2 at Underhill and the return fixture ended goalless. That was the last meeting between the two clubs as Orient were promoted to League One at the end of that season and have remained their since.