Introduction to Leyton Orient Legendary Players
The Legacy of Leyton Orient
Leyton Orient, based in East London, has a history dating back to 1881, making it one of the oldest football clubs in the capital.
The club has spent much of its existence moving between the second, third, and fourth tiers of English football, with a single season in the top flight in 1962–63. Despite not being a mainstay at the higher levels, Orient has cultivated a deep-rooted connection with its local community and developed a loyal following that has remained resilient through both successes and setbacks.
The Breyer Group Stadium, known colloquially as Brisbane Road, has hosted some memorable moments and iconic players over the decades, each leaving their mark in different eras and divisions.
Criteria for Ranking the Best Players
To compile this list, we considered a mix of appearances, impact, legacy, and importance to the club during key periods. While goals and trophies contribute to a player’s standing, so too does longevity, influence during pivotal promotions or relegation battles, and representation at international level when relevant.
This list spans generations—from mid-century greats to modern-day heroes—ensuring that players who shaped the club’s identity in different contexts are recognised. We’ve drawn on historical records, supporter perspectives, and verified statistics to ensure a balanced and factual ranking.
10. Jobi McAnuff (2014–2016, 2017–2021)
Jobi McAnuff brought vast experience and professionalism to Leyton Orient across two separate spells, first joining in 2014 following a successful stint at Reading. After a brief time away, he returned in 2017 and became a central figure in the club’s resurgence. McAnuff was a calming influence on and off the pitch during the O’s National League campaign, helping them win promotion back to the Football League in 2018–19. His versatility allowed him to play in midfield or wide areas, where his composure, vision, and work ethic were instrumental.
He captained the side under Justin Edinburgh and remained a vital presence during a turbulent period that included managerial changes and off-field restructuring. McAnuff also briefly took on interim managerial duties in 2021. With over 170 appearances for Orient, his leadership and dedication made him a respected figure at Brisbane Road and a vital part of the club’s modern identity.
9. Peter Kitchen (1977–1979, 1982–1984)
Peter Kitchen enjoyed two successful spells at Leyton Orient, first joining in 1977 from Doncaster Rovers. A sharp and instinctive centre-forward, Kitchen quickly established himself as a key player, scoring 28 goals in 65 league appearances during his initial stint. His goalscoring form was crucial in helping Orient reach the FA Cup semi-finals in 1977–78, one of the club’s most memorable modern achievements.
After a move to Fulham and then Cardiff City, Kitchen returned to Brisbane Road in 1982, continuing to find the net regularly. He added another 21 goals in 49 league appearances during his second spell, bringing his total to 49 league goals in 114 appearances for the club. Kitchen’s intelligence in front of goal, sharp movement, and ability to score under pressure made him a fan favourite. His contributions in two separate spells underline his importance in Orient’s late 1970s and early 1980s history.
8. Alan Comfort (1986–1989)
Alan Comfort was a dynamic left winger whose time at Leyton Orient left a lasting impression despite his relatively short stay. He joined the club in 1986 from Cambridge United and quickly became a key player, known for his pace, direct style, and eye for goal. Comfort scored 46 league goals in just 150 appearances for Orient, a remarkable return for a wide player and one that highlights his attacking influence.
His most memorable contribution came during the 1988–89 season, when his goals and creativity helped Orient secure promotion from the Fourth Division via the play-offs. He was widely admired for his ability to beat defenders and deliver with both feet, often creating chances from nothing. Sadly, injury forced him into early retirement at just 25 years old, shortly after moving to Middlesbrough. Despite this, Comfort’s time at Brisbane Road remains fondly remembered, particularly for his flair and match-winning contributions.
7. Dean Cox (2010–2016)
Dean Cox was a fan favourite at Leyton Orient, combining technical quality with a relentless work rate over six memorable seasons. Joining from Brighton & Hove Albion in 2010, Cox quickly became the creative heartbeat of the team, primarily operating as a winger or attacking midfielder. He made 235 league appearances and scored 45 league goals, regularly contributing assists thanks to his exceptional delivery and vision.
Cox played a pivotal role in Orient’s promotion push during the 2013–14 League One season, helping the team reach the play-off final, where they narrowly lost to Rotherham United on penalties. His ability to deliver from set-pieces, pick out teammates with precision, and score long-range efforts made him a consistent threat. Despite leaving the club in 2016 following ownership changes, Cox’s contributions remain deeply appreciated by supporters. His combination of flair and consistency ensures his place among Orient’s most influential modern-era players.
6. Laurie Cunningham (1974–1977)
Laurie Cunningham began his professional career at Leyton Orient after being released by Arsenal, and it was at Brisbane Road that his exceptional talent first began to attract national attention. A skilful and graceful winger, Cunningham made 75 league appearances for Orient, scoring 15 goals. His dribbling ability, pace, and flair stood out in the Third Division, and he quickly became a player fans recognised as having the potential to play at the very highest level.
In 1977, he earned a move to West Bromwich Albion, where he became one of the first black footballers to represent England at under-21 level. Cunningham’s legacy stretches beyond statistics—his success challenged racial prejudices and paved the way for future generations. His later move to Real Madrid made him one of the first English players to star abroad. Despite leaving Orient early in his career, his time there remains pivotal to his incredible football journey.
5. Sid Bishop (1953–1965)
Sid Bishop was a dependable and long-serving defender who played a crucial role in Leyton Orient’s most successful era. He joined the club’s ground staff in June 1952 and turned professional by the end of that year, making his senior debut in February 1954. Bishop went on to play 296 league matches, scoring four goals, and amassed a total of 323 senior appearances, placing him among an elite group of players to have reached that mark for the club.
Bishop featured in every match of Orient’s 1961–62 First Division promotion-winning campaign and was ever-present again the following season as the club competed at the top level for the only time in its history. Known for his calm defending, reliability, and positional sense, Bishop’s finest moment arguably came when he scored in a 2–1 win over Liverpool in May 1963. He left the club in 1965, remembered as one of Orient’s most loyal and consistent performers.
4. Stan Charlton (1952–1955, 1958–1965)
Stan Charlton was a composed and dependable full-back who enjoyed two influential spells at Leyton Orient. He first joined the club in 1952 and made a strong impression before moving to Arsenal in 1955. Charlton returned to Orient in 1958 and played a central role in the most successful period in the club’s history. In total, he made 367 league appearances for the club across both spells, captaining the side during their promotion to the First Division in 1961–62.
Charlton’s leadership at the back was crucial as Orient competed at the highest level the following season. He remained a first-team regular until his retirement in 1965, known for his consistency, positional awareness, and ability to organise the defence. Charlton’s influence extended beyond his playing ability; he led by example and was widely respected by teammates and supporters alike. His longevity and impact during Orient’s golden era secure his place among the club’s greatest players.
3. Matt Lockwood (1998–2007)
Matt Lockwood was one of the most effective and popular full-backs in Leyton Orient’s modern history. Joining from Bristol Rovers in 1998, he became a near ever-present at left-back for nine seasons, making 328 league appearances and scoring 50 goals — an exceptional record for a defender. His trademark left foot made him a threat from free-kicks and penalties, and he regularly contributed goals and assists throughout his time at the club.
Lockwood’s attacking instincts and stamina helped define Orient’s style during the early 2000s, and he was instrumental in their promotion from League Two in the 2005–06 season. He scored a hat-trick against Gillingham in 2006, one of the highlights of his career, and was named in the PFA Team of the Year multiple times. Lockwood’s balance of defensive responsibility and offensive output made him a standout performer over a long period, earning him a place among the O’s all-time greats.
2. Tommy Johnston (1956–1958, 1959–1961)
Tommy Johnston was Leyton Orient’s all-time greatest goalscorer, leaving an indelible mark in two prolific spells. Signed from Newport County in February 1956, he scored 70 league goals in 87 appearances before moving to Blackburn Rovers. He returned to Orient in February 1959 and netted 51 goals in 93 league matches. Overall, he scored 121 goals in just 180 league games for the club.
His 1957–58 season stands out: Johnston was joint top scorer in the Second Division with 43 goals for both Orient and Blackburn, propelling Orient’s attack. His powerful, instinctive striking ability and signature worn arm bandage made him instantly recognisable. In recognition of his enduring impact, the South Stand at Brisbane Road was renamed the Tommy Johnston Stand. His goal-scoring feats earned him the title of the club’s greatest player in a 1999 fan poll.
1. Peter Allen (1965–1978)
Peter Allen holds the record for most Football League appearances for Leyton Orient, amassing 432 league games during a 13-year spell at the club. Signed from West Ham United in 1965, Allen quickly became a first-team regular and remained a mainstay through several managerial changes and league campaigns. A versatile and committed midfielder, he also contributed 27 league goals and was known for his energy, intelligence, and reliability in possession.
Allen’s consistency was remarkable, and he often captained the side, earning widespread respect from teammates and fans. He played during a transitional period for the club and provided leadership and stability through both promotions and relegation battles. After retiring in 1978, Allen trained as a solicitor, showing the same dedication in his post-football career. His appearance record stands as a testament to his endurance, professionalism, and loyalty—qualities that define him as Leyton Orient’s greatest ever player.
Comparison of Leyton Orient Legends
Playing Styles and Contributions
The evolution of football across the decades is reflected clearly in the diversity of styles among Leyton Orient’s greatest players. For example, Stan Charlton, a full-back from the 1950s and 60s, was known for his leadership and positional discipline in a defensively structured era, whereas Matt Lockwood, a full-back from the late 1990s and 2000s, embodied the more modern attacking full-back, regularly contributing goals and assists from open play. Their roles reflect the tactical demands of their respective eras—Charlton’s focus on organisation and defence during Orient’s First Division campaign contrasts with Lockwood’s dynamic runs and set-piece prowess in the lower leagues.
Similarly, comparing a natural goal poacher like Tommy Johnston to a winger like Dean Cox highlights the shift in how attacking contributions are made. Johnston thrived in the Second Division with clinical finishing in and around the box, while Cox, in League One and League Two, created and scored with equal effectiveness from the flanks. These contrasts underline how success at Orient has taken many different forms depending on the era and level of competition.
Impact on Club Success
Many of these players were instrumental during significant high points in Orient’s history. Stan Charlton captained the team during their sole First Division campaign, while Peter Allen provided stability and leadership through a long stretch in the second and third tiers, becoming the club’s record appearance holder. Tommy Johnston’s goalscoring directly influenced Orient’s rise through the divisions in the 1950s, including a promotion push and an individual scoring record that remains unmatched.
In more recent times, players like Dean Cox and Matt Lockwood were central to Orient’s League Two promotion in 2005–06 and the subsequent play-off run in League One. Jobi McAnuff, meanwhile, helped guide the club back into the EFL in 2018–19, leading a squad that restored pride and stability following financial turmoil and relegation. Each of these players contributed in key moments, whether at the top of the Football League pyramid or battling for survival in the lower tiers.
Records and Achievements
Individual Honours and Awards
Several players on this list were recognised with individual accolades during their time at Brisbane Road. Matt Lockwood earned multiple selections in the PFA Team of the Year for League Two, reflecting his consistency and impact as an attacking defender.
Peter Allen was awarded a testimonial year in 1976 after breaking the club’s all-time appearance record. Tommy Johnston’s 121 goals remain a club record, and he was voted the greatest Leyton Orient player in a 1999 supporter poll—an accolade that further cements his legacy.
Club Milestones and Championships
Many of these legends played central roles in the club’s landmark achievements. Stan Charlton captained Orient during their 1961–62 promotion to the First Division, the highest level the club has ever reached. Sid Bishop played every match of that same campaign and remained ever-present in the top flight the following season.
Alan Comfort’s contributions were vital in the 1988–89 play-off success, while Jobi McAnuff’s leadership helped Orient return to the Football League in 2019 following National League promotion. From Johnston’s prolific scoring to Lockwood’s role in the 2006 promotion, these players are woven into the fabric of Leyton Orient’s proudest moments.
