Middlesbrough Quiz
A Middlesbrough quiz with answers: Juninho, Ravanelli, the 2004 League Cup, the 2006 UEFA Cup run and the Riverside. Instant scoring, no sign-up.
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easy
Middlesbrough were formed in 1876 by members of a local club in a different sport, looking for something to keep them fit through the winter. Which sport?
WhyThe founders came from Middlesbrough Cricket Club, meeting in a gymnasium behind the Albert Park Hotel on Linthorpe Road. -
easy
Middlesbrough moved into the Riverside Stadium in 1995 — which ground did they leave behind after 92 years?
WhyAyresome Park had been home since 1903, and its gates were famously padlocked during the 1986 financial collapse. -
medium
Academy graduate Stewart Downing left Middlesbrough in 2009 in a deal worth up to £12m — which club did he join?
WhyDowning moved to Aston Villa after relegation, later playing for Liverpool and West Ham. He returned to his boyhood club in 2015 for a reported £5.5m. -
medium
Middlesbrough lost the 1997 League Cup final after a replay. Which club beat them?
WhyRavanelli put Boro ahead in extra time at Wembley before Emile Heskey equalised in the 118th minute; Steve Claridge won the replay for Leicester. -
hard
After Middlesbrough's relegation from the Premier League in 1997, their Brazilian playmaker left for which Spanish club?
WhyAtlético Madrid took him to the Vicente Calderón, and it was from there that he returned to Teesside on loan in 1999-2000. -
medium
Which manager took Middlesbrough from the Third Division to the First in successive promotions in 1987 and 1988, months after the club had nearly ceased to exist?
WhyRioch worked without pay through the 1986 crisis, training his young squad in parks and schools, then led them up twice in two years. -
medium
Which Croatia international did Middlesbrough sign from Lazio in 2000?
WhyAlen Boksic arrived for around £2.5m in August 2000, aged 30, and top-scored in his first season with 12 Premier League goals. -
hard
Which midfielder had already lost two Champions League finals with Valencia before joining Middlesbrough in 2003?
WhyGaizka Mendieta lost the 2000 final to Real Madrid and the 2001 final to Bayern Munich on penalties. He arrived on loan from Lazio and the move was made permanent in 2004. -
medium
Fabrizio Ravanelli scored a hat-trick on his Middlesbrough debut on the opening day of 1996‑97, in a 3‑3 draw against which club?
WhyBoro came from behind three times at the Riverside, Ravanelli's treble starting with a penalty driven past David James. -
medium
Ravanelli arrived on Teesside in 1996 from the club he had just scored for in that year's Champions League final. Which club was it?
WhyHe opened the scoring for Juventus against Ajax in the 1996 final, then swapped Turin for Middlesbrough in a £7m deal that summer. -
hard
The last competitive match at Middlesbrough's old ground, in April 1995, was a 2‑1 win that sealed the Division One title. Who were the visitors?
WhyJohn Hendrie scored both goals — the last competitive goals at the old ground — as Boro went up as champions before the move across town. -
medium
Middlesbrough were docked three points in 1996‑97 for failing to fulfil a Premier League fixture, a deduction that ultimately sent them down. Which club were they due to play?
WhyBoro called off the December trip to Blackburn citing an injury and illness crisis; the appeal failed, and without the deduction they would have stayed up. -
medium
Which Brazilian midfielder did Middlesbrough sign in 1996 from Porto, only for him to go AWOL during his time on Teesside?
WhyEmerson had won back-to-back titles and the Portuguese player of the year award at Porto before his £4m move, and started brilliantly before disappearing. -
hard
Bernie Slaven, Middlesbrough's cult goalscorer of the late 1980s, was signed in 1985 for £25,000 from which Scottish club?
WhySlaven had been the Scottish league's leading scorer at Albion Rovers; on Teesside he won three promotions and later played for the Republic of Ireland. -
medium
Paul Gascoigne joined Middlesbrough in 1998 from which club?
WhyGascoigne left Rangers for Teesside as Boro pushed for promotion straight back to the Premier League. -
medium
Which former Middlesbrough defender retired as a player in 2006 and was immediately made the club's manager despite not holding a UEFA Pro Licence?
WhyGareth Southgate had captained the League Cup-winning side in 2004. The Premier League granted special dispensation in November 2006 on the grounds that his international career had left no time for the coaching courses. -
hard
Then club-record signing Afonso Alves scored a hat-trick in an 8‑1 home win on the final day of the 2007‑08 season — against which club?
WhyManchester City were dismantled at the Riverside in May 2008. Alves had arrived from Heerenveen that January for what was then a club-record fee of around £12.5m. -
medium
Which Middlesbrough striker scored the decisive late goal in both of the 2006 UEFA Cup comebacks, against Basel and Steaua Bucharest?
WhyMassimo Maccarone struck in the 90th minute against Basel and headed an 89th-minute winner against Steaua, both completing recoveries from three goals down on aggregate. -
medium
Locked out of their padlocked ground as the club fought liquidation, Middlesbrough staged their first home fixture of the 1986‑87 season at another club's ground. Which one?
WhyHartlepool United lent Boro their ground for the Port Vale game on 23 August 1986, three weeks after the gates were padlocked and thirty non-playing staff, Bruce Rioch among them, were sacked. -
hard
Mark Schwarzer joined Middlesbrough in 1997 and stayed 11 years — which English club did he sign from?
WhyThe Australian goalkeeper had only a brief spell at Valley Parade, arriving there from Kaiserslautern before the February 1997 move to the Riverside. He finally left Boro for Fulham in 2008. -
medium
Middlesbrough were founder members of the Premier League in 1992 but went straight back down. Which manager took them up in 1992 and was in charge for that relegation?
WhyLawrence's side finished runners-up in the old Second Division in 1992, then came 21st in the Premier League's first season, five points adrift of safety. -
easy
Which Australian striker did Middlesbrough sign from Leeds United in 2004?
WhyMark Viduka cost £4.5m and scored twice in the 4-1 second-leg win over Basel during the UEFA Cup run. He left for Newcastle United on a free in 2007. -
hard
Who scored the first competitive goal at the Riverside Stadium, in August 1995?
WhyHignett opened the scoring on the new ground's first afternoon in front of 28,286, and Fjortoft added the second. -
easy
In 1989 Middlesbrough sold Gary Pallister for £2.3m, at the time a British record fee for a defender. Which club bought him?
WhyPallister had just been relegated with Boro that summer; at Old Trafford he went on to form a title-winning centre-back partnership with Steve Bruce. -
easy
Which local businessman was part of the consortium that saved Middlesbrough from liquidation in 1986 and went on to become the club's chairman in 1994?
WhyGibson had founded the haulage firm Bulkhaul in his early twenties and joined the Boro board at 26, the youngest director in the club's history. -
hard
On the way to the 1997 FA Cup final, Middlesbrough were held 3‑3 at Old Trafford by which third-tier side before winning the semi-final replay?
WhyChesterfield, in the third tier that season, led 2-0 before Middlesbrough fought back to draw 3-3 after extra time; Boro won the replay at Hillsborough 3-0. -
easy
Who was Middlesbrough's manager for the 2006 UEFA Cup final against Sevilla?
WhySteve McClaren took charge in June 2001, and the Eindhoven final was his last game for Boro: the FA had named him England's next manager on 4 May, six days before the final, and he left the club on 11 May, the day after the 4-0 defeat. Robson (1994-2001), Southgate (appointed June 2006) and Strachan (2009-10) all managed Middlesbrough, but none of them was in the dugout that night. -
easy
Middlesbrough reached the 1997 FA Cup final and lost 2‑0 at Wembley to which club?
WhyRoberto Di Matteo scored inside the first minute — then the fastest goal in an FA Cup final at Wembley — and Eddie Newton added a second late on. -
easy
Which Brazilian, signed from São Paulo in 1995, went on to have three separate spells at Middlesbrough?
WhyJuninho Paulista cost £4.75m in October 1995 and became the symbol of the mid-1990s Boro side. He came back on loan in 1999-2000 and again permanently in 2002, winning the League Cup in his third spell. -
easy
Middlesbrough lifted the 2004 League Cup, the first major trophy in the club's history — which side did they beat 2‑1 in the final?
WhyBolton Wanderers were swept aside inside seven minutes at the Millennium Stadium, Joseph-Desire Job and Boudewijn Zenden scoring. Kevin Davies pulled one back after a Mark Schwarzer error. -
easy
Which former England captain took over as Middlesbrough's player-manager in 1994 and won the Division One title in his first season in charge?
WhyRobson left Manchester United in 1994 to take the job, made 22 league appearances himself, and took Boro straight up as champions.
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About Middlesbrough
Some clubs give you trophies. Boro gave you a decade you couldn't look away from — Juninho arriving from São Paulo in October 1995 for around £4.75m, Fabrizio Ravanelli scoring a hat-trick on his debut in a 3-3 draw with Liverpool, and a three-point deduction for the unfulfilled trip to Blackburn that sent the club down in 1996-97 after two cup finals in the same season. This quiz lives in that territory: the names, the transfers and the afternoons Teesside still argues about.
Start earlier if you like. Middlesbrough were formed in 1876 by members of Middlesbrough Cricket Club looking for something to keep them fit through the winter, and the club's modern story starts in 1986, when a consortium including Steve Gibson saved it from liquidation and Bruce Rioch — working without pay through the crisis — took a young side from the Third Division to the First in successive promotions in 1987 and 1988. Ayresome Park was home for 92 years before the move to the Riverside in 1995, where Craig Hignett scored the new ground's first goal in a 2-0 win over Chelsea.
Then the reward. The 2004 League Cup, beaten finalists Bolton Wanderers swept aside inside seven minutes at the Millennium Stadium, was the first major trophy in the club's history, and captain Gareth Southgate went from lifting it to managing the club in 2006 on special dispensation without a Pro Licence. Two seasons later came the run nobody scripts: three goals down on aggregate against Basel, then again against Steaua Bucharest, and Massimo Maccarone scoring the decisive late goal in both.
The questions are drawn fresh each time, so a second go isn't the same round. Answers come with a line of context — where the fee went, who scored, what it cost — which is usually where the argument starts. Play it on the bus, play it against a mate, and see how much of the Robson era you actually kept.
Middlesbrough quiz answers, explained
Every question from the quiz above. Play it first; each answer stays folded until you open it.
Middlesbrough were formed in 1876 by members of a local club in a different sport, looking for something to keep them fit through the winter. Which sport?
Show answer
Cricket. The founders came from Middlesbrough Cricket Club, meeting in a gymnasium behind the Albert Park Hotel on Linthorpe Road.
Middlesbrough moved into the Riverside Stadium in 1995 — which ground did they leave behind after 92 years?
Show answer
Ayresome Park. Ayresome Park had been home since 1903, and its gates were famously padlocked during the 1986 financial collapse.
Academy graduate Stewart Downing left Middlesbrough in 2009 in a deal worth up to £12m — which club did he join?
Show answer
Aston Villa. Downing moved to Aston Villa after relegation, later playing for Liverpool and West Ham. He returned to his boyhood club in 2015 for a reported £5.5m.
Middlesbrough lost the 1997 League Cup final after a replay. Which club beat them?
Show answer
Leicester City. Ravanelli put Boro ahead in extra time at Wembley before Emile Heskey equalised in the 118th minute; Steve Claridge won the replay for Leicester.
After Middlesbrough's relegation from the Premier League in 1997, their Brazilian playmaker left for which Spanish club?
Show answer
Atlético Madrid. Atlético Madrid took him to the Vicente Calderón, and it was from there that he returned to Teesside on loan in 1999-2000.
Which manager took Middlesbrough from the Third Division to the First in successive promotions in 1987 and 1988, months after the club had nearly ceased to exist?
Show answer
Bruce Rioch. Rioch worked without pay through the 1986 crisis, training his young squad in parks and schools, then led them up twice in two years.
Which Croatia international did Middlesbrough sign from Lazio in 2000?
Show answer
Alen Boksic. Alen Boksic arrived for around £2.5m in August 2000, aged 30, and top-scored in his first season with 12 Premier League goals.
Which midfielder had already lost two Champions League finals with Valencia before joining Middlesbrough in 2003?
Show answer
Gaizka Mendieta. Gaizka Mendieta lost the 2000 final to Real Madrid and the 2001 final to Bayern Munich on penalties. He arrived on loan from Lazio and the move was made permanent in 2004.
Fabrizio Ravanelli scored a hat-trick on his Middlesbrough debut on the opening day of 1996‑97, in a 3‑3 draw against which club?
Show answer
Liverpool. Boro came from behind three times at the Riverside, Ravanelli's treble starting with a penalty driven past David James.
Ravanelli arrived on Teesside in 1996 from the club he had just scored for in that year's Champions League final. Which club was it?
Show answer
Juventus. He opened the scoring for Juventus against Ajax in the 1996 final, then swapped Turin for Middlesbrough in a £7m deal that summer.
The last competitive match at Middlesbrough's old ground, in April 1995, was a 2‑1 win that sealed the Division One title. Who were the visitors?
Show answer
Luton Town. John Hendrie scored both goals — the last competitive goals at the old ground — as Boro went up as champions before the move across town.
Middlesbrough were docked three points in 1996‑97 for failing to fulfil a Premier League fixture, a deduction that ultimately sent them down. Which club were they due to play?
Show answer
Blackburn Rovers. Boro called off the December trip to Blackburn citing an injury and illness crisis; the appeal failed, and without the deduction they would have stayed up.
Which Brazilian midfielder did Middlesbrough sign in 1996 from Porto, only for him to go AWOL during his time on Teesside?
Show answer
Emerson. Emerson had won back-to-back titles and the Portuguese player of the year award at Porto before his £4m move, and started brilliantly before disappearing.
Bernie Slaven, Middlesbrough's cult goalscorer of the late 1980s, was signed in 1985 for £25,000 from which Scottish club?
Show answer
Albion Rovers. Slaven had been the Scottish league's leading scorer at Albion Rovers; on Teesside he won three promotions and later played for the Republic of Ireland.
Paul Gascoigne joined Middlesbrough in 1998 from which club?
Show answer
Rangers. Gascoigne left Rangers for Teesside as Boro pushed for promotion straight back to the Premier League.
Which former Middlesbrough defender retired as a player in 2006 and was immediately made the club's manager despite not holding a UEFA Pro Licence?
Show answer
Gareth Southgate. Gareth Southgate had captained the League Cup-winning side in 2004. The Premier League granted special dispensation in November 2006 on the grounds that his international career had left no time for the coaching courses.
Then club-record signing Afonso Alves scored a hat-trick in an 8‑1 home win on the final day of the 2007‑08 season — against which club?
Show answer
Manchester City. Manchester City were dismantled at the Riverside in May 2008. Alves had arrived from Heerenveen that January for what was then a club-record fee of around £12.5m.
Which Middlesbrough striker scored the decisive late goal in both of the 2006 UEFA Cup comebacks, against Basel and Steaua Bucharest?
Show answer
Massimo Maccarone. Massimo Maccarone struck in the 90th minute against Basel and headed an 89th-minute winner against Steaua, both completing recoveries from three goals down on aggregate.
Locked out of their padlocked ground as the club fought liquidation, Middlesbrough staged their first home fixture of the 1986‑87 season at another club's ground. Which one?
Show answer
Victoria Park, Hartlepool. Hartlepool United lent Boro their ground for the Port Vale game on 23 August 1986, three weeks after the gates were padlocked and thirty non-playing staff, Bruce Rioch among them, were sacked.
Mark Schwarzer joined Middlesbrough in 1997 and stayed 11 years — which English club did he sign from?
Show answer
Bradford City. The Australian goalkeeper had only a brief spell at Valley Parade, arriving there from Kaiserslautern before the February 1997 move to the Riverside. He finally left Boro for Fulham in 2008.
Middlesbrough were founder members of the Premier League in 1992 but went straight back down. Which manager took them up in 1992 and was in charge for that relegation?
Show answer
Lennie Lawrence. Lawrence's side finished runners-up in the old Second Division in 1992, then came 21st in the Premier League's first season, five points adrift of safety.
Which Australian striker did Middlesbrough sign from Leeds United in 2004?
Show answer
Mark Viduka. Mark Viduka cost £4.5m and scored twice in the 4-1 second-leg win over Basel during the UEFA Cup run. He left for Newcastle United on a free in 2007.
Who scored the first competitive goal at the Riverside Stadium, in August 1995?
Show answer
Craig Hignett. Hignett opened the scoring on the new ground's first afternoon in front of 28,286, and Fjortoft added the second.
In 1989 Middlesbrough sold Gary Pallister for £2.3m, at the time a British record fee for a defender. Which club bought him?
Show answer
Manchester United. Pallister had just been relegated with Boro that summer; at Old Trafford he went on to form a title-winning centre-back partnership with Steve Bruce.
Which local businessman was part of the consortium that saved Middlesbrough from liquidation in 1986 and went on to become the club's chairman in 1994?
Show answer
Steve Gibson. Gibson had founded the haulage firm Bulkhaul in his early twenties and joined the Boro board at 26, the youngest director in the club's history.
On the way to the 1997 FA Cup final, Middlesbrough were held 3‑3 at Old Trafford by which third-tier side before winning the semi-final replay?
Show answer
Chesterfield. Chesterfield, in the third tier that season, led 2-0 before Middlesbrough fought back to draw 3-3 after extra time; Boro won the replay at Hillsborough 3-0.
Who was Middlesbrough's manager for the 2006 UEFA Cup final against Sevilla?
Show answer
Steve McClaren. Steve McClaren took charge in June 2001, and the Eindhoven final was his last game for Boro: the FA had named him England's next manager on 4 May, six days before the final, and he left the club on 11 May, the day after the 4-0 defeat. Robson (1994-2001), Southgate (appointed June 2006) and Strachan (2009-10) all managed Middlesbrough, but none of them was in the dugout that night.
Middlesbrough reached the 1997 FA Cup final and lost 2‑0 at Wembley to which club?
Show answer
Chelsea. Roberto Di Matteo scored inside the first minute — then the fastest goal in an FA Cup final at Wembley — and Eddie Newton added a second late on.
Which Brazilian, signed from São Paulo in 1995, went on to have three separate spells at Middlesbrough?
Show answer
Juninho. Juninho Paulista cost £4.75m in October 1995 and became the symbol of the mid-1990s Boro side. He came back on loan in 1999-2000 and again permanently in 2002, winning the League Cup in his third spell.
Middlesbrough lifted the 2004 League Cup, the first major trophy in the club's history — which side did they beat 2‑1 in the final?
Show answer
Bolton Wanderers. Bolton Wanderers were swept aside inside seven minutes at the Millennium Stadium, Joseph-Desire Job and Boudewijn Zenden scoring. Kevin Davies pulled one back after a Mark Schwarzer error.
Which former England captain took over as Middlesbrough's player-manager in 1994 and won the Division One title in his first season in charge?
Show answer
Bryan Robson. Robson left Manchester United in 1994 to take the job, made 22 league appearances himself, and took Boro straight up as champions.
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