When greatness falters: Examining the worst losing runs of legendary coaches

No football manager has ever had it easy. Despite their celebrated tactical acumen and well-preparedness, even the most famous and successful managers in history have gone through times of struggle where the continuous pressure of succeeding as a professional football manager appeared intolerable. 

These rare episodes of difficulty highlight the erratic nature of professional football and the intricate interrelation among form, self-confidence, and outside challenges. 

This paper explores the longest losing and winless streaks these outstanding managers have gone through. It also examines the elements engendering these unusual declines as well as the techniques employed to overcome them. By doing this, football enthusiasts get a taste of the flexibility and fortitude that define their legacy. 

 Pep Guardiola (longest winless run: 7; worst losing streak: 5)

Despite his outstanding reputation as one of the most creative tacticians in the game of football, Pep Guardiola has faced some difficulties, including protracted losing streaks that tested his managerial approach and resolve. 

Beginning in October 2016, Guardiola's first season at Manchester City saw the team fail to secure a single victory in six straight games across all competitions. A devastating loss in the EFL Cup to Manchester United, as well as losses to presumably weaker Premier League teams like Everton and Southampton, defined this spell. 

The slump was brought on by the team's defensive shortcomings, poor offensive finishing, and players' natural adjustment period to the rigorous tactical approach of the Spanish coach. This stood in sharp contrast to the team's explosive 10-game season starting point. 

Manchester City endured a worse situation under Guardiola in 2024, when the team went winless for seven matches, including a record-setting five-match losing streak in all competitions between October and November, the worst string of defeats in Pep's career. Damaging losses to Tottenham and Brighton during this difficult period threw off City's rhythm. 

The physical toll of fighting on several fronts, injuries to important players, and roster changes just helped to worsen the situation. Nonetheless, Guardiola has constantly shown his tactical sense and mental toughness in the face of such challenges; he sees them as chances for adaptation and learning, which is a core idea guiding his managerial approach. 

 Jose Mourinho (longest winless run: 7; worst losing streak: 4)

Renowned for his psychological sense and pragmatic style, José Mourinho is among the most praised managers in football history. Adversity of great proportions tests his managerial techniques. 

During his tenure as Tottenham Hotspur manager, the club remained winless for seven games (February–June 2020) and suffered devastating losses to Chelsea and Leipzig in the Premier League and the Champions League, respectively. 

In this run, Mourinho would endure four straight defeats for the first time in his managerial career, all by one-goal margins, results that saw Spurs get eliminated from Europe's Premier continental competition and lose steam in the top four race of England's first division.

Spurs lost five of their six games in the next season during a pivotal period that highlighted the club's general unreliability and finally resulted in Mourinho's resignation by April, even if earlier in the season they had temporarily led the league. 

With an incredible nine losses in sixteen games, the 2015–16 Premier League champions—who had been reigning champions—saw their most severe winless and losing streaks under Mourinho's direction. Perhaps this was the most infamous era of difficulty for Mourinho. 

Further aggravating Chelsea's terrible drop decline—which was exacerbated by tactical rigidity, increasing tensions in the locker room, and a general drop in morale—was Mourinho's dismissal right in the middle of the season. Chelsea finished eighth. 

Over his career, Jose has shown extraordinary flexibility and tenacity, which has helped him to establish himself as among the most successful managers in the game. He has churned out European success for AS Roma and Manchester United. 

 Antonio Conte (longest winless run: 13; worst losing streak: 3)

Although Antonio Conte has largely fared well, he has also faced great difficulties. His very aggressive and combative approach defined his style throughout his second Chelsea season in the 2017–18 Premier League. In the previous season, Chelsea had won the league under the Italian. 

Two straight big losses, 3-0 to Bournemouth and 4-1 to Watford, however, revealed the squad's defensive weaknesses and poor morale during this stormy season. 

This drop in performance as well as claims of dispute between Antonio Conte and the club's management about strategic and transfer-related issues helped Chelsea's fifth-place result and lack of Champions League qualification to be explained. 

Though this is not Conte's longest losing run, which occurred in the 2021–22 season with Tottenham Hotspur, where he suffered three consecutive league defeats twice, this difficult period may have been his most damning since the success of the previous season came with great expectations. 

Even a season-ending FA Cup triumph against Manchester United could not ameloriate Chelsea's lack of consistency. 

Despite showing promise in his first few career games as manager, recording three wins as coach of Serie B side Arezzo, Antonio Conte would fail to secure a win in the following thirteen games, losing seven of them. This would eventually result in his sack in October 2006, just over two months after his first game. 

Notwithstanding these ups and downs, Conte's strict discipline and tactical clarity have helped him to be successful on many teams. He has, yet, also sometimes encouraged internal conflict.

 Jürgen Klopp (longest winless run: 16; worst losing streak: 7)

Jürgen Klopp, known for his aggressive high-pressing style and passionate leadership, experienced ups and downs during his time at Liverpool. He endured one of his least successful campaigns in 2020–21 when Liverpool's hitherto perfect home winning run was shattered by six consecutive home losses at Anfield from January to March of that year. 

The absence of Virgil van Dijk sapped the team's cohesiveness and energy, which under Klopp's leadership had become their signature and resulted in notable defensive instability. 

An added predicament was the team's reputation for home field advantage being undermined by the absence of supporters resulting from Covid-19. 

Still, Klopp proved he could motivate and bring his squad together in the face of seemingly insurmountable obstacles by masterminding an incredible recovery in the later stages of the season that guaranteed Liverpool's third-place finish and Champions League qualification.

Although admirable, this perseverance was insufficient to gloss over Klopp's inclination for prolonged seven-game or more winless streaks—five of which had occurred by 2017—a pattern that raises more worries than repose. 

The most severe of these streaks was in 2006–07, Klopp's second-to-last season with Mainz, when the team went winless in 17 straight games (August 19–December 16). 

After a brief period of stability, Mainz eventually faced relegation which resulted from a seven-game losing run from March 18 to May 5. 

Jürgen Klopp's worst losing run was in the 04/05 Bundesliga campaign, when Mainz 05 lost seven straight league matches, four of which were by two or more goals.

These events, especially the Mainz horrorshow, buttress Klopp's sensitivity to lengthy winless runs despite his ability to recover and inspire his clubs to success. 

 Carlo Ancelotti (longest winless run: 9; worst losing streak: 3)

Despite his triumphs in the Champions League, Carlo Ancelotti was sacked in 2019–20 soon after going through one of his toughest seasons at Napoli. Marked by erratic on-field performance, internal conflicts between players and management, and other contributing elements, this period was defined by a nine-game winless streak across all competitions. 

Similarly, conflicts with top players regarding his training approaches produced a hostile atmosphere at Bayern Munich during the 2017–18 season, which led to his sacking. 

Carlo has only ever lost three consecutive games thrice in his career, two of which came while managing in the Premier League with Everton in the 2020/21 campaign, his last season in England before he was infamously carted away by Real Madrid.

Ancelotti has won the Champions League, club football's most prestigious trophy, with AC Milan and Real Madrid, in addition to several domestic trophies across Europe, thus his amazing career shows his capacity to recover and thrive in the face of hardship. 

 Sir Alex Ferguson (longest winless run: 9; worst losing streak: 3)

Though his position at Manchester United seemed to be in jeopardy in the late 1980s, Sir Alex Ferguson overcame great obstacles, and his time there is among the most renowned in the annals of football. 

Ferguson's 1988–89 campaign was disrupted by a nine-match winless run, which caused some supporters to call for his resignation. The Scottish legend lost three games on the bounce on six different occasions, his worst consecutive string of defeats in his managerial career, all while in the dugout of the Red Devils.

Nonetheless, United under Ferguson experienced a turning point in the 1989–90 FA Cup third round when a 1-0 victory over Nottingham Forest set off a rebirth that resulted in an FA Cup triumph, laying the groundwork for a dynasty that would rule English football for many years. 

 Arsène Wenger (longest winless run: 10; worst losing streak: 5)

Revolutionary Arsenal manager Arsène Wenger, whose name is intertwined with attacking football, faced several challenges. Arsenal were eliminated from many competitions and deprived of a chance to challenge for the Premier League title by a six-game stretch without a win during the 1998–99 season. 

Wenger's dry runs at Arsenal never exceeded half a dozen games, but he once went 10 games without a win as manager of AS Nancy-Lorraine in 1986 and almost repeated the feat in Japan a decade later after Nagoya failed to record a victory in 9 games before arresting this slide with a thunderous 6-1 demolition of Shimizu S-Pulse.

Despite Arsène Wenger spotting a respectable record even during critical downturns as manager of the Gunners, he suffered four straight defeats for the first time with the club in the tail end of his last season in football management, just behind the rotten milestone of five consecutive losses he set in 1984 with AS Nancy-Lorraine, his debut campaign as a soccer coach.

Still, Arsenal and the Premier League will always have traces of Wenger's resilience and dedication to his footballing values, most especially shown during the "Invincibles" season of 2003–04. 

Although he will face similar difficulties later in his career, such as a seven-game losing run in away league games during the 2017–18 season, his legacy lives on.