Robinson is an attacking left-back who first trained at Melwood ahead of the Europa League clash with Benfica in March 2010. Robinson had been excellent for the u-18 team and made his first-team debut before even playing for the reserves! At just 16 years and 250 days, Robinson became the youngest-ever player to feature for Liverpool's first team when he came on as a substitute at Hull in the last Premier League game of the 2009/10 season on 9 May 2010. The previous record-holder was Max Thompson, who was 17 years and 129 days old when he played in the final League fixture of the 1973/74 season. Jerome Sinclair has since improved Robinson's record by 244 days on 26 September 2012. Robinson added just two more appearances to his name in 2010/11 in consecutive Premier Leagues matches in April when he replaced the injured Fabio Aurelio at Arsenal and played for nearly eighty minutes against Birmingham. Robinson signed an extension to his contract at the end of October 2011 even though competition for the left-back slot he prefers had been increased by the signing of Jose Enrique. Robinson made two starts in the 2011/12 season, in the League Cup matches at Exeter and Brighton.
After appearing only six times for Liverpool's first team in the first half of the 2012/13 season, Robinson moved on loan to Wolverhampton Wanderers for the rest of the season. He made eleven appearances in The Championship but he and his new colleagues were unable to prevent Wolves from being relegated for the second successive season. On his return to Liverpool he learned that he had been called up to the England Under-21 squad for the European Championships to be held in Israel in June 2013.
Early in August 2013, it was officially confirmed that Robinson would be spending the whole of the 2013/14 season on loan at Championship club Blackpool. He made 34 league appearances for Blackpool plus one each in the League Cup and FA Cup. He would have made more appearances had he not been sent off against Bournemouth in September. He was also sent off against Blackburn in October and Birmingham in February, which led to further suspensions. In the final days of the summer transfer-window of 2014, Robinson made a permanent move to Queens Park Rangers and was immediately loaned by Harry Redknapp to Huddersfield Town in the Championship. In March 2015 he suffered a serious knee injury leading to his loan spell being cut short. It restricted his appearances in 2015/16 to just one game. He struggled to put this behind him 2016/17, being substituted in six of his seven starts. However, in 2017/18 Robinson finally came good at Loftus Road, becoming the first-choice centre back, scoring twice in 31 appearances and earning a new contract offer. He declined this though and joined fellow Championship side Nottingham Forest where he continued to put previous troubles behind him. Robinson scored twice in 38 league games and captained the side towards the end of the season.
In January 2020, Robinson was back in the Premier League, joining Sheffield United on a two and a half year deal for an undisclosed fee. Their manager Chris Wilder told the BBC: "Jack can play comfortably in a couple of roles and we're delighted to add him to the group. He's got a fantastic attitude and he's ambitious to earn a place in the team.". Robinson had to bide his time and featured just once as an unused substitute prior to the suspension of the season due to Covid 19. When it resumed behind closed doors, he did make six appearances.