He finished the season with 11 appearances, after which we was offered a new contract which he accepted a month later. 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.
Macclesfield Town
He signed a new deal with the club until the end of the 2007-2008 season in December, and after making two appearances for the team that season he joined Conference National side Altrincham on loan. He made a further 20 appearances for Macclesfield after his return and was offered a new contract at the end of the season, which he subsequently signed. Kettering Town
In the summer of 2009, Jennings left Macclesfield to join Kettering Town.
Cambridge United
Jennings joined Cambridge United in summer 2010 from Kettering on a two-year deal for an undisclosed fee decided by a tribunal.
He made 43 first team starts in his first season with the club In his second season with The U"s, Jennings was named as vice-captain by new manager Jez George.
In January 2012, Jennings put pen to paper in a new deal keeping him at the club until the summer of 2014. Mansfield Town
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. Jennings was released by the Stags at the end of the 2013/14 season. Forest Green Rovers
On 3 June 2014, Jennings signed for Forest Green Rovers on a two-year deal.
A frustrating start to life at Forest Green saw him suffer an anterior cruciate ligament injury in pre-season training.
The injury kept him out of action for eight months, however he returned to make his debut in a 2014-2015 Conference National play-off semi-final second leg defeat against Bristol Rovers in front of 10,563 supporters.
Born in Manchester, Greater Manchester, Jennings joined the senior Macclesfield Town team in May 2006 from Manchester City, making his debut in a 1–0 victory against Walsall in the FA Cup as a 90th-minute substitute on 21 November 2006, this led to Jennings famously playing in Macclesfield Town"s 3rd Round FA Cup clash against Chelsea at Stamford Bridge in 2007 His League Two debut came in Macclesfield"s first league victory of the 2006-2007 as they defeated Rochdale 1–0 in December. His first appearance for Kettering came in a 2–1 away win over Forest Green Rovers on the opening day of the 2009-2010 season. His first goal for the club came in a 2–0 home win against Grays Athletic on 6 March 2010. He scored his first goal for the club on 22 August 2015 in a 3–1 home win against Lincoln City. He then scored twice in a 2–1 win against Bromley on 31 August 2015 to help Forest Green to a seventh straight win at the start of the 2015-2016 National League season. He also scored the equaliser in a game that Forest Green went on to win 3–1 against promotion rivals Dover on 14 November 2015.
