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Later that month, Cummings was loaned to League One leaders Luton Town. He scored his first goal for Luton on 6 April 2019, coming on as a substitute against Blackpool, netting an equaliser in the 86th minute with the game finishing 2–2.

On 2 September 2019, it was announced that Cummings had signed for League One side Shrewsbury Town for an undisclosed fee. He made his debut for the club on 14 September, coming on as a 68th-minute substitute for Daniel Udoh away at A.F.C. Wimbledon, and five minutes later, he scored the equaliser in a 1–1 draw. Cummings scored in wins against Southend United and Sunderland, but minor injuries and illnesses over Christmas 2019 meant he was largely used as a substitute during January 2020. On 26 January 2020, Cummings came off the bench to net twice in a 2–2 draw with world and European champions Liverpool in the FA Cup fourth round.

Cummings is of Australian descent due to his mother. In July 2019, Australia manager Graham Arnold said that he wanted Cummings to represent them, which could be done as he had only played two friendlies for Scotland. In September 2019, Cummings told The Sun newspaper he was considering switching from Scotland to Australia and had already spoken with Socceroos assistant manager Rene Meulensteen.

Cummings was loaned to Scottish Premiership side Rangers in January 2018 for the rest of the season, with Rangers holding an option to make the transfer permanent. He made his competitive debut for the club on 24 January, in a 2–0 win against Aberdeen. Cummings was one of four players to make their first appearance for Rangers in that game. He scored his first goal for Rangers four days later, in a 2–1 win at Ross County. On 4 March, Cummings scored a hat-trick for Rangers in a Scottish Cup quarter-final against Falkirk.

On 13 July 2018, Cummings moved on a season-long loan to EFL League One side Peterborough United. After a strong start, scoring six goals in his first five league games, Cummings began to struggle for goals and his loan was terminated by Peterborough on 30 January 2019.

He moved to Nottingham Forest in June 2017, but has not played regularly for their first team. Cummings was loaned to Rangers in January 2018, Peterborough United in July 2018 and Luton Town in January 2019. He made his first full international appearance for Scotland in November 2017.

During the 2016 close season, Cummings signed a new four-year contract with Hibs. Peterborough United offered Hibs £1.2 million for Cummings in August 2016, but this proposal was rejected. He netted the winner in a 1–0 win Tannadice on 10 March 2017, and in doing so became the first Hibernian player to score more than twenty goals in three successive seasons since Joe Baker between 1957 and 1961. On 15 April, Hibs clinched the title and achieved promotion back to the Scottish Premiership after beating Queen of the South 3–0 at Easter Road. Later that day, Cummings tweeted that they had fulfilled his promise to return the team to the top flight. Cummings was nominated by PFA Scotland in their Young Player of the Year and Championship Player of the Year awards for 2016–17.

Cummings signed a three-year contract with Nottingham Forest on 17 June 2017, moving for an undisclosed fee. As part of the deal Cummings former clubs Heart of Midlothian and Hutchison Vale were awarded a solidarity fee, due to his youth development. He scored his first goal for Forest on his debut in a 2–1 EFL Cup win against Shrewsbury Town on 8 August 2017.

Cummings played for the Scotland under-19 and under-21 teams. He received his first call-up to the senior Scotland squad in November 2017. He made his first full international appearance that month, in a friendly against the Netherlands.

Cummings won the SPFL Young Player of the Month award for September 2014, after his two goals helped Hibs to beat Rangers in Glasgow. On 16 February 2016, Cummings became the first Hibs player to score in four consecutive Edinburgh derbies for 42 years after scoring the winner against Hearts in a Scottish Cup 4th round replay. On 16 April 2016, Cummings missed a penalty kick with a Panenka attempt in the Scottish Cup semi-final against Dundee United, which ended goalless, although he later scored the winning kick in the penalty shoot-out. He then played the first 65 minutes of the final, assisting Anthony Stokes' opening goal as Hibs won 3–2 against Rangers.

Cummings grew up a Hearts fan and attended Tynecastle High School. He played for local boys team Hutchison Vale and then joined the Hearts youth program. After struggling with injuries, Cummings was released by Hearts in 2012. After an impressive season with Hutchison Vale he was signed by Hibernian in the summer of 2013. Cummings made his debut senior appearance for Hibernian in a Scottish Premiership match against Inverness Caledonian Thistle in November 2013. Cummings scored his first career goals on 21 May 2014, netting twice as Hibernian won 2–0 against Hamilton Academical in the first leg of the promotion/relegation play-off. Hibs lost the return match 2–0 and Cummings missed the decisive kick in the penalty shoot-out, which resulted in Hibs being relegated to the Scottish Championship.

Cummings started his professional career with Hibernian, making 16 appearances and scoring twice as Hibernian were relegated in the 2013–14 season. He was their top goalscorer over each of the next three seasons, scoring more than 20 goals each season, making him the first player to achieve this feat for over 50 years. These goals helped Hibs win the Scottish Cup in 2016 and promotion in 2017.

Jason Steven Cummings (born 1 August 1995) is a Scottish professional footballer who plays as a striker for Shrewsbury Town, and the Scotland national team.