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In January 2018 he joined Bolton Wanderers on loan until the end of the season. On 8 June 2018, it was announced that Flanagan would be released at the end of his contract.

Flanagan signed a two-year contract with Scottish Premiership club Rangers, managed by his former Liverpool teammate Steven Gerrard, in June 2018. On the 19th of May 2020, it was announced that Flanagan would be leaving the club.

Flanagan was arrested after admitting assaulting his girlfriend, Rachael Wall, in Liverpool City Centre on 22 December 2017. After pleading guilty, in January 2018 he was sentenced to 40 hours of unpaid work and a 12-month community order.

In December 2015, Flanagan returned to full training with the Liverpool first team squad. On 20 January 2016, he made his first appearance in a Liverpool matchday squad in 619 days, in a FA Cup third-round replay, coming off the bench as a 49th-minute substitute in a 3–0 victory over Exeter City. Seven days later, he started in a League Cup semi-final match against Stoke City, playing for 105 minutes. After Liverpool won on penalties, Liverpool manager Jürgen Klopp hailed Flanagan as his man of the match.

On 18 March 2016, Flanagan signed a new long-term contract through to 2019. On 20 March 2016, Flanagan captained Liverpool in a Premier League match against Southampton at St Mary's Stadium.

On 5 August 2016, Liverpool announced that Flanagan had joined fellow Premier League club Burnley on a season-long loan.

Flanagan did not make a single appearance for Liverpool during pre-season due to a buildup of fluid on the knee. Initially scheduled to return to first team training in early September, on 18 September Liverpool manager Brendan Rodgers confirmed that Flanagan had undergone corrective surgery on his left knee and would miss the opening months of the season. On 29 March 2015, Flanagan made his return from injury playing 30 minutes in a Liverpool All-Star charity match at Anfield. After scans highlighted a new problem, however, Flanagan underwent another knee operation in April, keeping him out for a further six-to-nine months. On 21 May 2015, Flanagan signed a 12-month contract extension with Liverpool to continue his rehabilitation.

On 4 June 2014, Flanagan made his England senior debut, replacing Alex Oxlade-Chamberlain in the second half of a friendly against Ecuador in the United States. For the 2014 FIFA World Cup, Flanagan was announced by Roy Hodgson as one of the standby players.

Flanagan continued his spell in the first team to cover for the long term injuries of Martin Kelly and Glen Johnson, making his second start the following weekend and playing the full match in a 1–1 draw at the Emirates Stadium against Arsenal, a match in which he accidentally knocked out stand-in captain Jamie Carragher through a clash of heads. The incident did not faze the 18-year-old, however, as he gave an assured performance. In the following home match, against Birmingham City, and playing alongside fellow Liverpool Academy graduate Jack Robinson, Flanagan again played the full 90 minutes and helped Liverpool to keep a clean sheet in a 5–0 win. His performance earned him a place in BBC Sport pundit Garth Crooks's Premier League team of the week.

Flanagan played the full 90 minutes in Liverpool's opening Premier League match of the season at home to Sunderland, a 1–1 draw. Flanagan played the full 90 minutes in Liverpool's 3–1 away win against Exeter City in the League Cup, and made a late substitute appearance away to Brighton & Hove Albion in the following round of the same competition. He made his 11th Reds appearance one week after his 19th birthday, replacing Fábio Aurélio in Liverpool's 5–1 win over Oldham Athletic in the third round of the FA Cup.

He returned to the team on 24 March against Wigan Athletic in the Premier League in the absence of injured duo Glen Johnson and Martin Kelly. Flanagan retained his place, playing the full 90 minutes in Liverpool's next two league matches, before being substituted for Brad Jones in the 26th minute against Blackburn Rovers after his short back-pass had led to goalkeeper Doni being sent off. Liverpool won the match 3–2.

On 19 September, Flanagan was one of the clutch of teenagers to travel to Switzerland to play Young Boys in a Europa League group match. Flanagan, however, was not named in the matchday squad. On 8 November, he made his first appearance of the season in the starting XI against Anzhi Makhachkala in the Europa League. He played the full 90 minutes in the 1–0 loss, played in Moscow. Flanagan struggled through the season with injuries and was forced to miss a significant number of matches for the under-21s.

Flanagan made his first start in the Premier League in 18 months in the club's away visit to Arsenal on 2 November, after illness forced Glen Johnson out of the squad. Johnson's illness, coupled with José Enrique's injury, led to Flanagan starting in the left back position in a reshuffled defence. Flanagan made his Merseyside derby debut, a 3–3 draw away at Everton, on 23 November in a performance that was praised by his teammate Steven Gerrard, who said that the Liverpool players gave Flanagan a round of applause when he came into the dressing room after the match. Flanagan retained his place at left back in the next match against Hull City and was again praised for his performance, despite the match ending in a 3–1 defeat, with manager Brendan Rodgers describing his performance as "outstanding". Flanagan scored his first goal for Liverpool with a powerful half volley in a 5–0 win away at Tottenham Hotspur on 15 December.

On 28 May 2013, Flanagan was named in manager Peter Taylor's 21-man squad for the 2013 FIFA U-20 World Cup. He made his debut on 16 June in a 3–0 win in a warm-up match against Uruguay. On 12 May 2014, he was named as one of seven reserves for England's 2014 FIFA World Cup squad and trained with the squad at their pre-tournament training camp in Portugal.

As Flanagan's only senior international appearance was in a friendly, he remains eligible for the Republic of Ireland through his grandparents. In November 2013, it was reported that Ireland manager Martin O'Neill wanted him to declare.

Flanagan has earned numerous plaudits for his style of play since his breakthrough into the Liverpool first team in November 2013; most notably, the World Cup-winning former Brazil captain and full back Cafu heralded Flanagan as his "successor", applauding his "speed, strength and determination" and stating he "has everything required to be one of the best full-backs in the world". This has led to fans dubbing Flanagan as "the Scouse Cafu".

Flanagan made his first team debut when he started the Premier League match against Manchester City at Anfield on 11 April 2011, being handed the number 38 shirt and playing at right back. Liverpool went on to win the match 3–0, with the 18-year-old playing the full 90 minutes.

In Flanagan's fifth start for Liverpool, he was employed as a left back against Fulham, with Liverpool winning 5–2. His next match, against Tottenham Hotspur, resulted in him conceding a controversial penalty for minimal contact on Spurs' Steven Pienaar. Liverpool lost the match 2–0, thus falling out of a UEFA Europa League spot with one match left of the season, one point behind Tottenham. Flanagan was awarded young player of the 2010–11 season for his consistent contribution at right-back. He was delighted to receive this award, and said there were a number of names that helped him to progress so much. He quoted after receiving the reward, "I would first of all like to thank the gaffer, Dalglish. He believed in me, and decided I was good enough for the starting line up, and I couldn't wish for a better manager to play under." On 8 July 2011, Flanagan signed a new long-term contract with Liverpool.

In May 2011, Flanagan was called up to the England under-19 squad for the first time, although he had to withdraw due to a calf injury. In August 2011, he was named in the provisional squad for England's 2013 Under-21s qualifying matches for the first time. He made his debut in the 6–0 win over Azerbaijan.

While still in the U18 team, Flanagan made his reserve debut at Hull City in March 2010. Promoted to the reserve team at the start of the 2010–11 season, he first featured in the Lancashire Senior Cup triumph over Oldham Athletic. He was subsequently picked out as one of the reserve team to watch by The Times sport writer Tony Barrett.

Jonathon Patrick Flanagan (born 1 January 1993) is an English professional footballer who plays as a full back for Scottish Premiership club Rangers. Flanagan started his career with Liverpool, and has also played for Burnley and Bolton Wanderers. He has played in one full international match for the England national team, in 2014.