Club captain Alex Mowatt was one of the most significant departures as he left following the expiration of his contract and is now playing for Championship rivals West Brom.
Loan star Daryl Dike fast became a fan favourite as his goals fired the Tykes into the play-offs but an agreement was not able to be reached to make his stay in West Yorkshire permanent.
In total, 14 players left the club - either permanently or on loan - so we did some digging to find out how they are getting on away from Oakwell.
1. Alex Mowatt
Alex Mowatt - The midfielder has featured in 12 of West Brom's 14 Championship games this season, scoring three goals to help the club sit third in the table. Photo: Getty Images
2. Conor Chaplin
Conor Chaplin - The forward left Barnsley for League One Ipswich and has scored four goals and provided two assists in eight appearances. He has been in fine form in recent weeks, claiming three goals and one assist in his last four outings. Photo: Getty Images
3. Elliot Simoes
Elliot Simoes - The winger made his debut for Barnsley in 2019 after joining the club from FC United of Manchester. He spent time on loan at Doncaster Rovers last season before making the switch to French side Nancy. Photo: Getty Images
4. Michael Sollbauer
Michael Sollbauer - The defender made 18 starts in all competitions following his arrival in South Yorkshire in 2019-20 and featured 43 times in Barnsley’s Championship play-off season in 2020-21. However, he joined German second division side Dynamo Dresden in the summer to be closer to his family and is a regular starter for the club. Photo: Getty Images