Chelsea Quiz Questions and Answers

42 Chelsea questions in rounds of ten, with the answers kept separate so you can read them out. Free to use for a pub quiz, a matchday WhatsApp group or your own revision — no sign-up, and the page prints cleanly.

Round 1 Round 2 Round 3 Round 4 Round 5

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Round 1

  1. Chelsea's very first nickname wasn't 'The Blues' — what were they originally called, inspired by the war veterans living next door?
  2. Chelsea won their first-ever Champions League in 2012 in the most dramatic way. Whose 88th-minute header forced extra time before he buried the winning penalty?
  3. Who scored the only goal as Chelsea beat Manchester City in the 2021 Champions League final in Porto?
  4. Roman Abramovich's takeover in 2003 launched a spending spree. Who is generally regarded as his very first signing for Chelsea?
  5. In 2003 Chelsea fans voted on the club's greatest-ever player. Who won, nicknamed the 'Magic Box', beating out Osgood and Chopper Harris?
  6. Which manager won Chelsea's first-ever league title in 1955 — and was the first man to win the English top flight as both a player and a manager?
  7. Peter Osgood, the 'King of Stamford Bridge', had his ashes interred at the club in 2006. Where exactly were they buried?
  8. At the new Club World Cup final in 2025, Chelsea stunned the favourites 3-0. Which team did they dismantle?
  9. For 35 years until 1968, another popular spectator sport ran every week around the edge of Chelsea's Stamford Bridge pitch, sharing the ground with the football. What was it?
  10. Which Chelsea striker's transfer from Liverpool in January 2011 cost a then British-record £50m but is remembered as a famous flop?
Answers — round 1
  1. The Pensioners — The crest featured a Chelsea pensioner until manager Ted Drake scrapped it in the 1950s — the name nods to the red-coated retired soldiers of the nearby Royal Hospital Chelsea.
  2. Didier Drogba — It was his final kick for the club before leaving — equaliser and shootout winner in Bayern's own stadium, the 'Final in Munich'.
  3. Kai Havertz — It was his first-ever goal in the competition — Mount's through-ball sent him one-on-one with Ederson under Thomas Tuchel.
  4. Glen Johnson — The young right-back arrived from West Ham for £6m that July, the opening shot of a summer that also brought Makélélé, Crespo, Joe Cole and Duff.
  5. Gianfranco Zola — The diminutive Italian wizard dazzled for seven years at the Bridge; the vote came just as Abramovich's era was beginning.
  6. Ted Drake — He'd won titles as a player with Arsenal; at Chelsea he axed the 'Pensioner' crest and nickname, ushering in 'The Blues'.
  7. Under the penalty spot at the Shed End — The 'Wizard of Os' also has a bronze statue outside the West Stand and was the last player to score in every round of the FA Cup (1970).
  8. Paris Saint-Germain — Cole Palmer scored twice and João Pedro added a third before half-time at MetLife Stadium in New Jersey.
  9. Greyhound racing — The dogs circled the perimeter of the live football pitch from 1933 to 1968; the ground had even hosted a speedway team nicknamed the 'Pensioners' a few years before that.
  10. Fernando Torres — He scored just one goal in his first 14 Premier League games for the club after the deadline-day move, never recapturing his Anfield form.

Round 2

  1. In a 2002 FA Cup tie against Norwich, Gianfranco Zola scored one of the most outrageous goals in Chelsea history when he met a Graeme Le Saux corner first-touch at the near post. How did he finish it?
  2. In 1997 Chelsea won the FA Cup with the fastest-ever Wembley final goal at the time, after just 42 seconds. Who scored it?
  3. Which goalkeeper went on a then-Premier League record run of 1,025 minutes without conceding during Chelsea's 2004-05 title-winning season?
  4. Which Chelsea defender captained the club to the 2012 Champions League but was suspended for the final, then controversially lifted the trophy in full kit anyway?
  5. Chelsea's 1970 FA Cup triumph over Leeds was so brutal it's still cited as football's dirtiest final. How was that famous title finally decided?
  6. Which flamboyant Dutchman became Chelsea's first foreign manager in 1996 and won the FA Cup in his only full season as player-manager?
  7. What is the name of the famous terraced stand at Stamford Bridge that gave its name to the club's most vocal supporters?
  8. Frank Lampard set a remarkable Premier League record for an outfield player between 2001 and 2005. What was it?
  9. Which Chelsea manager, sacked in 2007 despite huge success, returned for a second spell in 2013 and declared himself 'The Happy One' on his comeback?
  10. Chelsea won their first-ever European trophy in 1971, the season after lifting the FA Cup. Beating Real Madrid in a replayed final, which trophy did they win?
Answers — round 2
  1. A backheel flick, sending the ball behind his own body into the net — He met it in mid-air and flicked it behind his body 'like it was under remote control' — a defining image of Zola's cult-hero genius.
  2. Roberto Di Matteo — His thunderbolt against Middlesbrough set the tone; 15 years later the same man managed Chelsea to their first Champions League title.
  3. Petr Čech — That season Chelsea conceded just 15 league goals all campaign — still a Premier League record — as Mourinho's side stormed to the title.
  4. John Terry — A red card in the semi-final at Barcelona ruled him out, but he changed into his playing strip to join the celebrations in Munich.
  5. A replay at Old Trafford — After a 2-2 draw at Wembley, the rematch went to extra time before Chelsea won 2-1, with Osgood and David Webb the heroes.
  6. Ruud Gullit — He coined the phrase 'sexy football' for his attacking style before being sacked mid-1998, replaced by Vialli, who promptly won three trophies.
  7. The Shed End — The original covered terrace housed the hardcore 'Shed Boys'; though redeveloped, the Shed End name lives on at the southern end of the ground.
  8. 164 consecutive league appearances — His incredible run of never missing a league game over several seasons spoke to both his durability and importance to the side.
  9. José Mourinho — On returning he joked he was no longer 'The Special One' but 'The Happy One' — before a famously sour exit during the 2015-16 title defence.
  10. European Cup Winners' Cup — They beat Real Madrid in a replayed final near Athens for the club's first European silverware — they'd win the same trophy again in 1998.

Round 3

  1. In which season did Chelsea win their first-ever Premier League title, kicking off a period of dominance?
  2. Didier Drogba, a twice-returning Chelsea talisman, represented which nation at international level?
  3. Chelsea sold Eden Hazard in 2019, ending seven brilliant years at the club. Which side did he join?
  4. Chelsea signed Cole Palmer, who became their talismanic playmaker, in 2023 from which club?
  5. Which Italian manager won the Premier League in his debut Chelsea season of 2016-17?
  6. Chelsea's 2009-10 title-winning side set a club record for goals in a Premier League season with how many?
  7. Whose stoppage-time header won Chelsea the 2013 Europa League final against Benfica in Amsterdam?
  8. In the 2012 Champions League semi-final at Camp Nou, which Chelsea midfielder scored a stunning chip over Víctor Valdés?
  9. Gianluca Vialli's Chelsea won which European trophy in 1998, beating Stuttgart 1-0 in the final?
  10. Which manager led Chelsea to the 2019 Europa League title before departing to become Juventus boss?
Answers — round 3
  1. 2004-05 — José Mourinho's first season in charge ended a 50-year wait for a top-flight title, with a then-record miserly defence.
  2. Ivory Coast — He was the Elephants' captain and all-time top scorer while starring for Chelsea in the Abramovich era.
  3. Real Madrid — The Belgian moved to the Bernabéu that summer, having just won the Europa League as his Chelsea farewell.
  4. Manchester City — The young forward left the Etihad for Stamford Bridge and immediately became Chelsea's penalty-taking star.
  5. Antonio Conte — He switched to a 3-4-3 mid-season and stormed to the title before winning the FA Cup the following year.
  6. 103 — They battered Wigan 8-0 on the final day to break 100 — the free-scoring peak of Carlo Ancelotti's first year.
  7. Branislav Ivanović — The Serbian defender met Juan Mata's corner in the 92nd minute after Torres had opened the scoring.
  8. Ramires — The Brazilian's delicate lob just before half-time was pivotal to Chelsea's famous away-goals survival against Barcelona.
  9. European Cup Winners' Cup — Gianfranco Zola scored seconds after coming on as a substitute in Stockholm; it was the same trophy Chelsea first won in 1971.
  10. Maurizio Sarri — His only Chelsea season ended with a 4-1 win over Arsenal in the Baku final before he returned to Italy.

Round 4

  1. Which manager won the Premier League and FA Cup Double in his debut Chelsea season, 2009-10?
  2. Chelsea won the 2012 FA Cup final at Wembley, beating which team 2-1 through Ramires and Drogba?
  3. Which defensive midfielder did Chelsea sign from Real Madrid in 2003, giving his name to a specialist holding role?
  4. Chelsea were founded in 1905 by which businessman, who owned the Stamford Bridge athletics ground?
  5. Who holds Chelsea's club record for goals in a single league season, netting 41 in 1960-61?
  6. Which striker won the Premier League Golden Boot twice as a Chelsea player, in 2006-07 and 2009-10?
  7. In 2018 Chelsea signed which goalkeeper for a then world-record fee for a keeper, around £71m?
  8. Chelsea's 2004-05 title winners set a Premier League points record for the era. How many points did they finish on?
  9. Which unpopular interim manager led Chelsea to the 2013 Europa League title and a top-four finish?
  10. In May 2013 Frank Lampard became Chelsea's all-time leading scorer, passing a total that had stood for 47 years. Whose club record did he break?
Answers — round 4
  1. Carlo Ancelotti — The Italian, wearing his trademark raised eyebrow, delivered Chelsea's first-ever league-and-cup Double.
  2. Liverpool — It came days before their Champions League triumph, capping a remarkable end to Roberto Di Matteo's caretaker spell.
  3. Claude Makélélé — The Frenchman's screening play in front of the back four became so iconic it was dubbed the 'Makélélé role'.
  4. Gus Mears — He created the club to fill his stadium after Fulham declined to rent it, and Chelsea joined the Football League a year later.
  5. Jimmy Greaves — The teenage prodigy plundered 41 First Division goals before leaving for AC Milan, a Chelsea single-season mark never beaten.
  6. Didier Drogba — He hit 20 to top the charts in 2007 and a huge 29 in the 2010 Double season, dominating both title campaigns.
  7. Kepa Arrizabalaga — The Spaniard arrived from Athletic Bilbao as Courtois left for Real Madrid, breaking the goalkeeper transfer record.
  8. 95 — Mourinho's first champions racked up a then-record 95 points, a mark unbeaten until Manchester City's 100 in 2018.
  9. Rafael Benítez — Appointed 'interim' to fan protests after Di Matteo's sacking, he still delivered European silverware against Benfica before leaving.
  10. Bobby Tambling — Tambling had held the record since the 1960s with 202 goals; Lampard's 203rd came at Aston Villa and he finished on 211.

Round 5

  1. In December 2012 Chelsea became the first club in Champions League history to suffer which fate?
  2. Which midfielder won the Premier League in consecutive seasons with two different clubs — Leicester City in 2016 and Chelsea in 2017?
Answers — round 5
  1. Being eliminated in the group stage as reigning champions — Chelsea won their last group game 6-1 against Nordsjælland but still went out behind Juventus and Shakhtar Donetsk, months after winning the trophy.
  2. N'Golo Kanté — Kanté joined Chelsea from the newly crowned champions Leicester in 2016 and was named PFA Players' Player of the Year for 2016-17.

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