Windass played youth football for Huddersfield Town, spending ten years with the club.[4] He was released in April 2012 and trialled with Bradford City that same month.[5] Windass began his senior career with non-league team Harrogate Railway Athletic in December 2012.[6] He played on a semi-professional basis, combining his football career with a job as a construction labourer.[4]
He signed a professional contract with Accrington Stanley in July 2013.[7][8] He made his professional debut on 9 November 2013, in the FA Cup.[9] In November 2015 he turned down a new contract from the club on the advice of his father.[10] 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.[11] The duo agreed pre-contracts with Rangers later that month, ahead of the 2016–17 season.[12]
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.[13] 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.[14] His official debut was against Motherwell in the Scottish League Cup on 16 July[15] and Windass netted his first goal for the club against Lowland Football League side East Stirlingshire six days later.[16] Windass spent periods of the first half of the 2016–17 season on the sidelines due to a recurring hamstring injury in early August[17] and October.[18] 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.[19]
During the 2017–18 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 and Morelos.[20]
Windass joined Sheffield Wednesday on loan for the remainder of the 2019–20 season on 31 January 2020.[22] Due to COVID-19 his loan spell was extended until the end of July.[23]
On 2 September 2020, he made his move to Sheffield Wednesday a permanent signing for an undisclosed fee.[24][25] His first appearance on his return to the club was on 5 September 2020, in the EFL Cup away to Walsall, where he came on as a second-half substitute.[26] He would score his first goal as a permanent Wednesday player, on the opening day of the season in an away win against Cardiff City.[26] He would win the clubs player of the month competition during his first month back at the club, after scoring 2 goals in 5 appearances. [27] Following relegation to League One, Windass was heavily linked with moves back to the Championship, with the club rejecting offers in the region of £1 million for him.[28]
During pre-season for the 2021–22 season, Windass suffered a hamstring injury during a friendly against West Bromwich Albion which would rule him out for two months and the start of the League One season.[29] Despite being injured, he signed a new two-year deal at the club on 10 August 2021, which would see him remain at the club until the summer of 2023.[30][31] Following his injury, he returned to the squad on 20 November as an unused substitute against Accrington Stanley[32] and made his playing come back a few days later, coming off the bench to score an injury time winner against Milton Keynes Dons.[33] Following the end of the 2021–22 season, there was again interest in him, with his ex Rangers manager Pedro Caixinha linking him with a surprise move to Atlético Talleres reported.[34]
He scored two braces, against Cambridge UnitedinLeague One and Newcastle United in the FA Cup, resulting in him winning the club's player of the month for January 2023[35] and a nomination from the EFL for player of the month.[36] His form for the 2022–23 season, saw him and teammate Barry Bannan make the EFL League One team of the Season.[37]
He scored the only goal in the last minute of the League One play-off final against Barnsley to gain promotion to the Championship.[38][39] Wednesday exercised an option in his contract for him to remain at the club for another season.[40]
His goal against Blackburn Rovers, a looping chip from range that dropped under the crossbar won the April Championship Goal of the Month.[41][42] Following the end of the 2023–24 season, the club offered Windass a new contract.[43] He signed his new contract on 2 July 2024.[44]
