Jack Obersteller started with Millwall and had also been at Wycombe Wanderers by the time he had a single season with Exeter City. He later had a lengthy spell at Welling United.
Jack was a member of the Millwall youth system from the age of nine and became a scholar/trainee in 2005. After a brief period on loan at Crawley, Jack joined Wycombe Wanderers in 2007 where - just as at Millwall - he failed to make the first-team but did manage a dozen games in the Conference when loaned to Grays Athletic.
Released by Wycombe the nineteen-year-old Jack, who could play at left-back or left midfield, agreed a one-year deal with the Grecians in May 2008. Making his debut in a 4-1 win at Macclesfield Town in September 2008, Jack was only to start three League Two games for the Grecians whilst coming on as a substitute on four other occasions. His final game for the club was at Gillingham in January 2009.
Leaving City in May 2009, Jack’s seven games for the club proved to be his only appearances ever in the Football League as various trials with other clubs proved unsuccessful. He signed for Grays in September 2009 and moved to Welling United two months later where he remained until the end of the 2013/14 season.