A native of
Newcastle, Jennings began playing football at the age of seven with local team Hamilton Azzurri. As a teenager, he moved to one of the region's biggest clubs in
Adamstown Rosebud, and eventually made his senior debut at the age of 16. In 1978, he earned his first representative cap with Northern New South Wales, and after impressive displays for the Australian youth team later that year, he joined
Sydney Olympic in the
National Soccer League .
Sydney Olympic Playing initially as an attacking winger, Jennings' first season with Olympic witnessed relegation from the NSL, but he played a key role in helping the club achieve promotion in 1980. The arrival of
Manfred Schaefer to Pratten Park resulted in a move to left-back, a position he would make his own for the remainder of his career. After consecutive finals appearances with Olympic in 1984 (losing in the Grand Final to
South Melbourne) and 1985, Jennings transferred to rivals
Sydney Croatia.
Sydney Croatia Jennings tasted success immediately with Croatia, helping them claim the Minor Premiership in the Northern Conference in 1986. He played in all but two games for the club in 1988, as Croatia stormed their way into the Grand Final only to lose to
Marconi-Fairfield in a penalty-shootout. After a disappointing season the following year, he moved to
A.P.I.A. Leichhardt.
A.P.I.A. and Newcastle Jennings was an ever present in the A.P.I.A squad, but once the club was demoted from the NSL, he returned to his hometown, firstly with Adamstown Rosebud and then with the
Newcastle Breakers in 1993–94, where he played in every game but one in what proved to be his final season at national club level. He returned to Adamstown Rosebud for the remainder of the 1994 New South Wales Super League season, retiring from football upon its conclusion. ==International career==