A 4-year youth association with Stalybridge Celtic between 2005 and 2009 proved the impetus behind Connor's introduction to the first team squad in 2009. He made his senior debut on 3rd March 2009 and went on to score 3 goals by the end of that campaign. His second season ended with an 11-goal tally and he notched up 18 goals in the following 2010-11 season. In total, Connor scored an impressive 51 goals in 123 appearances for Stalybridge and made an appearance for the England 'C' side in November 2011 in recognition of his sterling performances.
A January 2012 move to Scunthorpe United yielded just 16 first team appearances and he was loaned out 3 times during his 2-year contract, to Stockport County, Macclesfield Town and Grimsby Town respectively. Whilst his spells with Stockport and Grimsby saw Connor score just 5 goals in a combined 25 games, his spell at Macclesfield was much more memorable, scoring 14 goals in just 16 games.
Signing for Wrexham in 2014, Jennings was made captain by Gary Mills in the 2015-16 season. He embraced the pressure of the role and finished the season as the Club's top scorer with 13 goals.
In the summer of 2016, Connor followed his former Wrexham teammate Jay Harris to Tranmere, signing a 2-year deal with Rovers. His first season at Prenton Park was, at times, frustrating as injury and a short loan spell at Macclesfield Town hampered his ability to play regular first team football. In spite of these setbacks, Jennings still managed 26 appearances for Rovers, scoring 8 goals that included a hat-trick in the 9-0 win over Solihull Moors and Tranmere's only goal in the 3-1 defeat to Forest Green Rovers in the 2017 National League Play-off Final.
After the disappointment of that 2017 defeat, Jennings had a much more prosperous 2017-18, making 46 appearances and scoring 8 goals. Connor was an important player throughout the season, however he was especially crucial to the cause during December 2017, scoring 6 goals in 4 games as Tranmere won all 4 matches of the month. For his efforts, Jennings was named National League Player of the Month for December 2017.
Jennings' fighting spirit also shone through in the 2018 National League Play-off Final, playing as a first-half substitute as one of the 'Wembley Warriors' just days after being hospitalised with illness.
The fan favourite, whose catchy “We've got Connor Jennings” chant will forever be associated with the return to the Football League in 2018, was rewarded for his performances with a new 2-year contract in May 2018, keeping the iconic midfielder at Tranmere until the end of the 2019-20 campaign.
He added to his Tranmere legend with a further 55 appearances and 13 goals in 2018-19. However, perhaps none will have meant more than his winning goal in the 119th-minute of the 2018-19 League Two Play-off Final, a goal that saw Tranmere beat Newport County 0-1 after extra time and return to the third tier after a 5-year absence.
Interesting Fact: Connor has been involved (scored or assisted) in goals in each of Tranmere's visits to Wembley under Micky Mellon. He scored in 2017 and 2019, whilst he assisted in 2018.