[11][12] He made his debut in a 2–1 victory over Northwich Victoria on 1 January 2008 and finished this spell with nine appearances before being recalled by Macclesfield in February.

[20] Jennings joined Cambridge United in summer 2010 from Kettering on a two-year deal for an undisclosed fee decided by a tribunal.

[23] On the final day of the transfer window, 31 January 2013, Cambridge United allowed Jennings to join Mansfield Town.

Jennings signed an 18-month contract with The Stags, with some media outlets mentioning that a fee was involved, with some stating it was a free-transfer.

[24] A frustrating start to life at Forest Green saw him suffer an anterior cruciate ligament injury in pre-season training.

[25] The injury kept him out of action for eight months, however he returned to make his debut in a 2014–15 Conference National play-off semi-final second leg defeat against Bristol Rovers in front of 10,563 supporters.

[39] In July 2022, Jennings was appointed to the newly created role of Head of Professional Player Support at Stockport County having continued to be involved at the club since his retirement twelve months prior.