The 1998–99 season was legendary for Manchester United, as Sir Alex Ferguson’s side won the historic treble. In the Premier League, United edged Arsenal by a single point, powered by the attacking brilliance of Dwight Yorke, Andy Cole, Ryan Giggs, and David Beckham. In the FA Cup, they beat Newcastle 2–0 in the final, with goals from Teddy Sheringham and Paul Scholes. The crowning moment came in the UEFA Champions League final against Bayern Munich, where dramatic stoppage-time goals from Sheringham and Ole Gunnar Solskjær sealed a 2–1 victory. This season cemented United’s place in football history as one of the greatest teams ever.

The 2003–04 season was highly disappointing for Real Madrid. Under Carlos Queiroz, the club finished 4th in La Liga, well behind champions Valencia. Despite a star-studded squad, including Zinedine Zidane, Ronaldo Nazário, Luís Figo, and David Beckham, inconsistency plagued the team. In the UEFA Champions League, Madrid were eliminated in the Round of 16 by Monaco, while in the Copa del Rey, they exited early against Real Zaragoza. Injuries and tactical issues undermined the squad, and internal tensions affected morale. The season highlighted that even a galaxy of stars could underperform without cohesion and balance, prompting significant reflection for the following years.

The 2007–08 season was turbulent for Real Madrid under Bernd Schuster. In La Liga, they finished 1st, winning the title after a tight race with Barcelona, led by Raúl, Ruud van Nistelrooy, and Gonzalo Higuaín. In the UEFA Champions League, Madrid were eliminated in the Round of 16 by AS Roma, and in the Copa del Rey, they exited in the Round of 16 as well. The season showcased strong domestic performance but European disappointments, emphasizing a squad with attacking talent yet occasional defensive fragility.

The 2014–15 season was a mixed campaign for Real Madrid under Carlo Ancelotti. They finished 2nd in La Liga, 2 points behind Barcelona, with Cristiano Ronaldo leading the scoring charts. In the UEFA Champions League, Madrid were eliminated in the semi-finals by Juventus, despite impressive performances from Gareth Bale and Karim Benzema. The club won the FIFA Club World Cup, adding international silverware, and also claimed the UEFA Super Cup by defeating Sevilla. However, they lost the Copa del Rey final to Barcelona. The season showcased attacking brilliance but highlighted defensive fragility, signaling the need for tactical adjustments moving forward.

The 2006–07 season saw Real Madrid finish a disappointing 7th in La Liga under Fabio Capello, failing to challenge for the title. Despite signings like Robinho and Thomas Gravesen, consistency eluded the squad. In the UEFA Champions League, they reached the Round of 16 but were eliminated by Bayern Munich, highlighting defensive vulnerabilities. The Copa del Rey campaign ended in the Round of 16 against Sevilla. Ronaldo Nazário’s fitness struggles limited his impact, while Raúl remained a key contributor. Overall, the season was marked by underperformance, managerial tension, and a need for squad restructuring, prompting a rethink for the following campaign.

Under Zinedine Zidane, Real Madrid won La Liga, finishing 3 points ahead of Barcelona, and claimed the UEFA Champions League, defeating Juventus 4–1 in the final to secure their 12th European title. The squad featured stars Cristiano Ronaldo, Karim Benzema, Gareth Bale, and Sergio Ramos, blending attacking firepower with experience and tactical discipline. Madrid scored freely in domestic and European competitions, with Ronaldo finishing as the season’s top scorer. They were eliminated early from the Copa del Rey by Celta Vigo. The season highlighted Zidane’s tactical flexibility and Real’s ability to dominate both domestically and in Europe.

Under Zinedine Zidane, Real Madrid achieved a historic feat by winning La Liga and successfully defending their UEFA Champions League title, securing a record 13th European crown with a 3–1 victory over Liverpool in the final. The squad, led by Cristiano Ronaldo, Gareth Bale, Karim Benzema, and Sergio Ramos, combined explosive attacking power with defensive resilience. In La Liga, Madrid finished 17 points ahead of Barcelona, dominating domestically. They were eliminated in the Copa del Rey round of 16 by Leganés. This season cemented Real Madrid’s status as a European powerhouse under Zidane’s leadership.

Under Carlos Queiroz, Real Madrid finished 4th in La Liga, struggling to compete with Valencia and Barcelona. The squad included Raúl, Zinedine Zidane, Ronaldo, Roberto Carlos, and emerging talents like David Beckham, blending individual brilliance with inconsistent team cohesion. Madrid’s attacking prowess was evident, but defensive frailties and tactical rigidity led to dropped points in crucial fixtures. In the Copa del Rey, they were eliminated early, and in the Champions League, they failed to progress past the quarter-finals, losing to Bayern Munich. The season highlighted the challenge of integrating Galáctico stars into a balanced, winning system.

Under Jorge Valdano, Real Madrid won La Liga, reclaiming domestic dominance. The squad featured stars such as Raúl, Fernando Hierro, Roberto Carlos, Davor Šuker, and Predrag Mijatović, blending emerging talent with experienced internationals. Madrid’s style combined attacking flair with solid defensive organization, allowing them to score freely while controlling key matches. In the Copa del Rey, they reached the latter stages but fell short, and in European competition, they exited early in the UEFA Cup. This season marked the rise of Raúl as a club icon and reinforced Madrid’s status as Spain’s top team domestically.

Under Vanderlei Luxemburgo, Real Madrid struggled to maintain domestic dominance, finishing 2nd in La Liga, behind Barcelona. The squad featured Ronaldo, Raúl, Zinedine Zidane, Roberto Carlos, and David Beckham, a blend of superstars and aging veterans. Inconsistency plagued league performance, with defensive lapses and underwhelming collective play costing crucial points. In cup competitions, Madrid were eliminated early in both the Copa del Rey and Champions League, highlighting tactical and squad issues. Despite individual brilliance from Ronaldo and Zidane, the season was largely disappointing. It underscored the need for tactical cohesion and squad rejuvenation to compete with Barcelona’s rising dominance.

Under Vicente del Bosque, Real Madrid finished 2nd in La Liga, narrowly missing out on the title to Real Sociedad. The squad featured stars like Raúl, Fernando Hierro, Roberto Carlos, Fernando Redondo, and Steve McManaman, blending experienced internationals with emerging talent. Madrid displayed attacking flair and tactical organization, scoring freely in key matches but dropping points inconsistently. In the Copa del Rey, they were eliminated in the quarter-finals, while in the Champions League, Madrid reached the quarter-finals but fell to Bayern Munich. The season reinforced Madrid’s domestic strength while highlighting the challenge of translating dominance into European glory.