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In January 2020 he moved on loan to Sheffield Wednesday.

During the 2017–18 Rangers F.C. season Windass finished the season with 18 goals in all competitions, tied (with Alfredo Morelos) as the club's top scorer for the season; with 13 of Windass' strikes in the league, the third-highest total behind Kris Boyd of Kilmarnock and Morelos.

Windass joined Rangers on 1 July 2016, signing a four-year contract alongside fellow Accrington player Matt Crooks. Both players had already been training with the club before completing their transfers after Rangers agreed a compensation fee with Accrington, reported to be around £60,000 per player. Windass made his debut for Rangers in a pre-season friendly against American side Charleston Battery on 7 July 2016, scoring the opening goal in a 2–1 win. His official debut was against Motherwell in the Scottish League Cup on 16 July and Windass netted his first goal for the club against Lowland Football League side East Stirlingshire six days later. Windass spent periods of the first half of the 2016–17 season on the sidelines due to a recurring hamstring injury in early August and October. Despite this, Windass was linked with a return to England in December 2016, with EFL Championship sides Derby County and Newcastle United reportedly showing an interest in the midfielder.

He signed a professional contract with Accrington Stanley in July 2013. He made his professional debut on 9 November 2013, in the FA Cup. In November 2015 he turned down a new contract from the club on the advice of his father. In January 2016 Accrington announced that Scottish club Rangers had approached Windass and teammate Matt Crooks directly, due to them being in the final six months of their contracts. The duo agreed pre-contracts with Rangers later that month, ahead of the 2016–17 season.

Windass played youth football for Huddersfield Town, spending ten years with the club. He was released in April 2012 and trialled with Bradford City that same month. Windass began his senior career with non-league team Harrogate Railway Athletic in December 2012. He played on a semi-professional basis, combining his football career with a job as a construction labourer.

Joshua Dean Windass (born 9 January 1994) is an English professional footballer who plays as a attacking midfielder for Sheffield Wednesday on loan from Wigan Athletic. He can also play as a forward.