On 6 April 2009, it was confirmed that de Jong signed a contract for three years with an option for another year with Twente.
His contract would start on 1 July 2009.
He played his first minutes for Twente in the cup match against SC Joure where he came on as a second-half substitute replacing Dario Vujičević.
He provided two assists in the 8–0 victory over SC Joure.
He scored his first two goals for Twente in the cup match against Capelle.

De Jong made his Europa League debut against FC Sheriff Tiraspol replacing Miroslav Stoch.
He also played against Fenerbahçe S.K. when he came on as a substitute.
He scored two goals in the cup match against Helmond Sport, Twente would go on and win the match 3–0.
In the away game against FC Utrecht de Jong made his debut in the Eredivisie when he replaced Kenneth Perez in the 90th minute.

Because Blaise N'Kufo was injured, de Jong deserved a starting spot against Werder Bremen in the knockout stage (32 teams) of the Europa League.
He scored his first goal in the Europa League for Twente in the away game against Werder Bremen.
Twente were already 3–0 behind when de Jong headed the 3–1 past goalkeeper Christian Vander.

De Jong scored his first Eredivisie goal for Twente in the home game against NEC at 28 February 2010.
Twente won this game with 2–1.
He scored his second Eredivisie goal in the home game against SC Heerenveen at 10 April 2010 in injury time, the matched finished 2–0.

He was very important in the 2010 Johan Cruyff Shield scoring the winning goal against Ajax in the eighth minute.
He started the match because Marc Janko was injured.
De Jong intercepted a pass from Maarten Stekelenburg to Gregory van der Wiel and then stayed calm and scored the winner in the match which ended 1–0.

De Jong played in the Champions League play-off game against Benfica, a 2–2 home draw on 16 August.
Four days later he scored his first Eredivisie goal of the campaign in a 5–1 demolition of SC Heerenveen.
The following week, on de Jong's 21st birthday, he found the back of the net two more times as Twente smashed VVV Venlo 4–1.

De Jong scored two goals against RKC Waalwijk on 21 January 2012, one was a tap in to an open goal and the other a penalty, as Twente ran out 5–0 winners.
In Twente's following fixture against FC Groningen on 29 January, de Jong netted a hat-trick, each goal coming off an assist from Ola John, and provided an assist for Leroy Fer as his side won 4–1 and climbed to second in the Eredivisie table.
On 10 February, de Jong found the back of the net two more times but Twente missed the chance to go top of the league table, as they lost 3–2 to SC Heracles.
De Jong's two goals meant he had scored seven times in the past three Eredivisie fixtures.

On 4 March, de Jong scored a goal in Twente's 6–2 thrashing of fellow title contenders PSV Eindhoven at the Philips Stadion.
Four days later in a Europa League match against Schalke 04, de Jong was the protagonist of a controversial penalty simulation that resulted in a red card for Schalke defender Joël Matip, and a penalty kick which he himself successfully converted, to ensure the win for his side by 1–0.
However Twente ended up falling out of the competition, losing 4–1 in the second leg in Germany, as de Jong's fellow Dutchman Klaas-Jan Huntelaar netted a hat-trick.

De Jong scored twice in two minutes on 14 April to put his side 2–1 up away to NAC Breda, but an injury-time strike from Nourdin Boukhari denied Twente the chance to close the gap on title rivals Ajax.
He finished the season with 25 goals on a joint-second place, seven behind top-scorer Bas Dost.
At the end of the 2011–12 season, De Jong announced he wanted to leave the club.
Having attracted the interest of several clubs around Europe, including Premier League side Newcastle United, de Jong accused the club's chairman [Joop Munsterman] of increasing the asking price for him.
In response, the club's chairman and Steve McClaren expressed dismay over de Jong's comments.
On 6 April 2009, it was confirmed that de Jong signed a contract for three years with an option for another year with Twente. His contract would start on 1 July 2009. He played his first minutes for Twente in the cup match against SC Joure where he came on as a second-half substitute replacing Dario Vujičević. He provided two assists in the 8–0 victory over SC Joure. He scored his first two goals for Twente in the cup match against Capelle.
De Jong made his Europa League debut against FC Sheriff Tiraspol replacing Miroslav Stoch. He also played against Fenerbahçe S.K. when he came on as a substitute. He scored two goals in the cup match against Helmond Sport, Twente would go on and win the match 3–0. In the away game against FC Utrecht de Jong made his debut in the Eredivisie when he replaced Kenneth Perez in the 90th minute.
Because Blaise N'Kufo was injured, de Jong deserved a starting spot against Werder Bremen in the knockout stage (32 teams) of the Europa League. He scored his first goal in the Europa League for Twente in the away game against Werder Bremen. Twente were already 3–0 behind when de Jong headed the 3–1 past goalkeeper Christian Vander.
De Jong scored his first Eredivisie goal for Twente in the home game against NEC at 28 February 2010. Twente won this game with 2–1. He scored his second Eredivisie goal in the home game against SC Heerenveen at 10 April 2010 in injury time, the matched finished 2–0.
He was very important in the 2010 Johan Cruyff Shield scoring the winning goal against Ajax in the eighth minute. He started the match because Marc Janko was injured. De Jong intercepted a pass from Maarten Stekelenburg to Gregory van der Wiel and then stayed calm and scored the winner in the match which ended 1–0.
De Jong played in the Champions League play-off game against Benfica, a 2–2 home draw on 16 August. Four days later he scored his first Eredivisie goal of the campaign in a 5–1 demolition of SC Heerenveen. The following week, on de Jong's 21st birthday, he found the back of the net two more times as Twente smashed VVV Venlo 4–1.
De Jong scored two goals against RKC Waalwijk on 21 January 2012, one was a tap in to an open goal and the other a penalty, as Twente ran out 5–0 winners. In Twente's following fixture against FC Groningen on 29 January, de Jong netted a hat-trick, each goal coming off an assist from Ola John, and provided an assist for Leroy Fer as his side won 4–1 and climbed to second in the Eredivisie table. On 10 February, de Jong found the back of the net two more times but Twente missed the chance to go top of the league table, as they lost 3–2 to SC Heracles. De Jong's two goals meant he had scored seven times in the past three Eredivisie fixtures.
On 4 March, de Jong scored a goal in Twente's 6–2 thrashing of fellow title contenders PSV Eindhoven at the Philips Stadion. Four days later in a Europa League match against Schalke 04, de Jong was the protagonist of a controversial penalty simulation that resulted in a red card for Schalke defender Joël Matip, and a penalty kick which he himself successfully converted, to ensure the win for his side by 1–0. However Twente ended up falling out of the competition, losing 4–1 in the second leg in Germany, as de Jong's fellow Dutchman Klaas-Jan Huntelaar netted a hat-trick.
De Jong scored twice in two minutes on 14 April to put his side 2–1 up away to NAC Breda, but an injury-time strike from Nourdin Boukhari denied Twente the chance to close the gap on title rivals Ajax. He finished the season with 25 goals on a joint-second place, seven behind top-scorer Bas Dost. At the end of the 2011–12 season, De Jong announced he wanted to leave the club. Having attracted the interest of several clubs around Europe, including Premier League side Newcastle United, de Jong accused the club's chairman [Joop Munsterman] of increasing the asking price for him. In response, the club's chairman and Steve McClaren expressed dismay over de Jong's comments.
Luuk de Jong