The 26-year-old was a product of the Owls’ academy but made just five senior appearances for the first team in his time at Hillsborough, scoring one goal and providing no assists, with all of those coming in the 2017/18 Championship season.
The versatile midfielder, who can also play at right-back, had previously spent time on loan with Bury, Accrington Stanley and Gillingham and looked set for a bright future with the Yorkshire club.
However, he made the somewhat surprising decision to join Hearts in 2018, as he confirmed upon his signing that there was interest from elsewhere, saying: “There has been interest from England in the Premier League and the Championship.
“I really took my time on the decision, but even before I came up I knew that Hearts was a massive club and you’ve got really passionate fans and a great fanbase, people who you want to play for so that really attracted me to come up.”
Clare’s time in Scotland was the most successful of his career so far, as he made 71 appearances for the Jam Tarts, contributing 12 goals and six assists.
During his spell with Hearts, he won the praise of his then-manager Craig Levein, who said: “I think we’re starting to see, particularly his ball carrying, he’s fantastic at breaking from midfield. He’s not been in a position to score yet but I think that will just be a matter of time.”
Another League One move occurred during the summer of 2021 as Clare made the permanent switch to Charlton Athletic. He has been a regular with the Addicks ever since, making 60 appearances in which he has contributed two goals and five assists, including a screamer against league leaders Plymouth earlier in the season.
Now aged 26, Clare has established himself as an experienced option at a top League One side as both a right-back and central midfielder, so he could have been an excellent option for Darren Moore to have in his squad.
If he continues to progress with Charlton, then the Owls will definitely rue the fact that Clare rejected their contract offer in 2018 before leaving on a free transfer.