But a late own-goal from Mathieu Baudry and a Carl Baker effort resulted in the east Londoners exiting the competition.
History books written on the club by its historian Neilson N Kaufman suggest that the choice of the name Orient came about at the behest of a player (Jack R Dearing) who was an employee of the Orient Shipping Company, later part of P&O - Pacific and Orient. The club's name was changed again to Clapton Orient in 1898 to represent the area of London in which they played, though there was another team called Clapton F.C.
Alberto Cavasin is getting ready to manage at Brisbane Road for the first time
O’s assistant manager Andy Edwards discusses reformed competition and strength of the east Londoners squad
“It gives us an opportunity to play a few players that haven’t had many minutes and we’ll certainly do that.”
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The Brisbane Road outfit will take part in the newly reformed English Football League Trophy next Tuesday (August 30) – previously the Johnstone’s Paint Trophy.
Stevenage make the trip to E10 this evening for the opening clash of the newly reformed EFL Trophy.
O's manager frustrated to end first home game with defeat
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The O’s shocked the west Londoners 2-1 at Craven Cottage that day with Craig Easton and Joe Keith on target.
Orient's golden years were in the 1960s and 1970s. In the 1961–62 season Orient were promoted to the top tier of English football, the First Division (now the FA Premier League), for the only time in their history, after finishing second in Division Two under the management of Johnny Carey. The team struggled in the top flight and were relegated from the top division the following season. Nonetheless, they did defeat local rivals West Ham United at home.
2007–08 was better, as Orient finished 14th with 60 points. The Os began the season in fine form, not dropping out of the top seven until after Christmas. However a loss of form in the second half of the season, recording only three wins from the last 12 games, meant the season ended in a respectable mid-table finish.
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Andy Hessenthaler believes Leyton Orient’s English Football League Trophy Southern Group G match tonight has come at just the right time.
They were Division Three champions in the 1969–70 season and spent the whole of the 1970s in Division Two. In 1972 Orient achieved one of the most famous results in their history – coming back from 2–0 down to beat Chelsea 3–2 in the FA Cup 5th round. They were also the Anglo-Scottish Cup Runners up 1976–77. In 1978 Orient were defeated in the semi final of the FA Cup, the furthest they have progressed in that competition.
Find out how Sammy Moore, Michael Clark, Josh Doherty, Freddy Moncur and Sam Roach have been getting on at other clubs over the past week
The draw for the English Football League Trophy, previously named the Johnstone’s Paint Trophy, was made this morning and Leyton Orient have been placed in Southern Group G.
Notable fans include Bob Mills, Daniel Mays, Andrew Lloyd Webber, and Andrew's brother Julian. The album Variations, which was famously used as the theme tune for London Weekend Television's South Bank Show, was written by Andrew Lloyd Webber as the result of his losing a bet to Julian Lloyd Webber on the result of a Leyton Orient match. Julian later presented a gold disc of Variations to the club chairman at half time during a game with Leicester City.
The O’s tasted defeat for the third time at Brisbane Road this season on Saturday at home to Mansfield Town.
No fixtures have been released as of yet so O’s fans will have to wait and see if they could make a trip to Brighton midweek.
The club finally reverted to "Leyton Orient" in 1987, shortly after Tony Wood took over as chairman and at a time when a supporters' campaign was taking place in the Leyton Orientear fanzine to reinstate the Leyton part of the club's name.
Italian reflects on 1-0 defeat to Portsmouth and Liam Kelly’s injury at Brisbane Road
Russell Slade was appointed manager of the club in 2010 and was successful in maintaining the club's League One status. Leyton Orient finished seventh, one place away from the playoff positions, in both the 2010–11 and 2012–13 seasons. In the 2013–14 season, Slade led Orient to the League One Play-Off final at Wembeley, where they lost to Rotherham United on penalties. Slade resigned on 24 September 2014 in order to join Cardiff City, and in 2015 Leyton Orient were relegated to League Two.
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“But I’ll carry on working with the players to get them better and hopefully we can get on a decent run.”
Leyton Orient were Division Three South champions in the 1955–56 season and spent 20 of the next 25 years in the Second Division, before being relegated at the end of the 1981–82 season. They have not been back to that level since.
History was made on Saturday 30 April 1921 when the Prince of Wales, later to become King Edward VIII, visited Millfields Road to see the O's play Notts County. The Orient won 3–0 and this was the first time a member of royalty had attended a Football League match. The royal visit was to show gratitude for Clapton Orient's patriotic example during the Great War and there is now a plaque erected on the site of the Millfields Road Stadium to commemorate this historic event.
Orient's main rivals are Southend United, after a period of Southend being Orient's geographically closest league rivals between 1998 and 2005. Although they have not often played in the same division, they have met in the League Cup in 2011–12 season, Leyton Orient beating United after extra time on penalties. More recently, the Shrimpers beat Orient 3–2 on aggregate in the 2012–13 Football League Trophy Southern Area Final.
Andy Hessenthaler’s team will face League Two rivals Stevenage, who now have Jobi McAnuff in their ranks, and take on local rivals Southend United.
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If Orient were to visit the Seagulls, it would see Dean Cox return to the club where he started his professional career.
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They’ve won just two times in all competitions, at home to Stevenage and on the road at Grimsby Town, and sit 10th in the table.
BBC Sport picks out this weekend's main talking points, results and tweets from the Football League.
Last week the east Londoners confirmed Martin Brennan was their new goalkeeper coach and he’ll be looking forward to the draw.
Leyton Orient boss Alberto Cavasin loses his first game in charge as Christian Burgess seals the points for Portsmouth.
Routine errors allowed the Stags to take the points and a lack of cutting edge in the final third resulted in just one goal for the hosts.
If a match finishes as a draw, both sides will receive one point each, but a penalty shoot-out will take place and the winner will earn an extra point.
“For us, as a smaller club, I think it is an opportunity to go and win it and get to Wembley. That is how I see it.