Merseyside-born Jennings began his career with Liverpool before joining Tranmere Rovers at the age of 15.
In total during his first season, the then-18-year-old made 32 appearances while scoring six goals from out wide, including a stunning brace in Tranmere’s 4-2 triumph over the Dons in October 2010.
The same month saw Jennings receive the PFA Apprentice of the Month award and later in the season he was also named League 1 Apprentice of the Year.
In July 2011, Jennings moved to German giants Bayern Munich where he would play for their reserve side in the Regionalliga Sud.
The winger made 36 appearances during his time in Europe before returning to England with then-Championship outfit Barnsley in August 2013.
Jennings featured 27 times for the Tykes during his first season at Oakwell while also spending a month on loan with the Dons, where Jennings impressed during his six appearances.
Last season, Jennings added another 24 games to his name to take his career total in English football to 89 heading into 2015/16.