Leyton Orient Trophies & Titles

It is perhaps a sign of how big a city London actually is that there are a number of different football clubs that exist in it and yet have never even come close to winning the top-flight title. Leyton Orient fit into that bracket, with the achievements of the Os being much smaller in scale. They are arguably a really good example of why it is that you have to take each and every trophy at its own merit, given that it might not mean anything to a big club but would mean the world to a smaller one. A side like Arsenal or Chelsea might not celebrate winning League Two, but Leyton Orient supporters most certainly did.

They have also come close winning bigger competitions, like the Second Division and the FA Trophy, only to miss out at the final moment. Those season might be seen as being worth little merit to Tottenham Hotspur fans, but the supporters of the Os will have loved every minute of coming close only to end up without a trophy to win. There are very few trophies to win in football, so those that you can be on the receiving end of are very much worth writing home about. In the case of Leyton Orient, the club’s successes are ones that they are extremely proud of, so we have written about them here accordingly.

League Titles

Leyton Orient have never won the Premier League and have not even coming close to doing so. They also didn’t win it when it was known as the First Division. In fact, the closest that they have come to enjoying any real sort of success was in the 1961-1962 season when they finished as runners-up in the Second Division.

What made that achievement all the more noticeable was that they gained promotion alongside the winners, which were Bill Shankly’s Liverpool. The Reds, of course, would go on to become the most successful club in England, whilst the Os time in the top-flight was short-lived indeed. They have, though, won some of the lower divisions.

Third Division South / Third Division

In the English Football League pyramid, the division that is on the third level has undergone numerous alterations over the years. For a time it was split into North and South, with Leyton Orient winning the Third Division South. Then later it became just the Third Division, before briefly being known as the Second Division when the First Division became the Premier League and the Second Division became the First Division.

Nowadays, of course, it is known as League One, although neither of the wins that the Os enjoyed came during the modern era. Here is a look at Leyton Orient’s success in the Third Division, including how many points they got, which team came second and how many points the second place team managed:

Season	Points	Second Place	Second Place Points
1955-1956	66	Brighton & Hove Albion	65
1969-1970	62	Luton Town	60

Fourth Division / League Two

The fourth tier in the English game has been just as liable to daft naming scenarios as the third tier, which can be demonstrated by the fact that it was known as the Fourth Division when Leyton Orient were promoted out of it as play-off winners in 1989. They also gained promotion thanks to a third place finish in the 2005-2006 season, at which point it was known as League Two.

It was also League Two when they won it for the first time in the club’s history, gaining promotion to League One as a result. Here is a look at Leyton Orient’s fourth tier title wins, alongside the points total that they managed and the team that finished second, alongside the points total of those runners-up:

Season	Points	Second Place	Second Place Points
2022-2023	91	Stevenage	85

National League

It is worth pointing out that a team like Leyton Orient hasn’t spent its entire existence in the Football League. Instead, the club has enjoyed a period playing non-league football, with the win that it enjoyed in the fifth tier of the English Football League being one of the most crucial in its entire existence.

This is because it allowed the Os to get back into football proper, rather than competing in the tier below it. Here is a look at how Leyton Orient have won the National League, including information about the club that finished second:

Season	Points	Second Place	Second Place Points
2018-2019	89	Solihull Moors	86

Cups & Trophies

As well as winning lower tier leagues, Leyton Orient supporters have also been able to cheer on their club in some lesser-known cups over the years. They wouldn’t register on the radar of the big Premier League teams, but for a side like the Os they present a chance to support the club and see the players lift some silverware. The club has come close to winning some trophies, such as in the 2018-2019 season when they lost 1-0 to AFC Fylde in the FA Trophy final.

Similarly, the Os ended up as runners-up to Nottingham Forest in the 1976-1977 Anglo-Scottish Cup, losing 5-1 on aggregate over two legs. Here is a look at the trophies that Leyton Orient have won, including information about the opposition and the score if it is available:

*When the club won the London Challenge Cup for the first time, they did so under the name of Clapton Orient Football Club.

**The 1971-1972 London Challenge Cup final originally ended 1-1, needing a replay to decide the winners. The club hadn’t yet gone through its merger and was known simply as Orient at the time.

***The club was also known as Orient when it defended its title a year later.

****In one of those curious quirks of fate that happen from time to time, the result of the Dubonnet Cup in 1911 was exactly what it would be the following year in the London Challenge Cup, will the side known as Clapton Orient then too.