Vanstrattan started his career for Central Coast and then Northern Spirit in Sydney. At just 17 he made his 1st grade debut for the Spirit, playing the last 3 games of the season for the National Soccer League club.
In summer 2001, he was signed by Juventus on a 5-year deal and loaned to Verona in a co-ownership deal for 500 million lire. At Verona, aged 19, Vanstrattan was a regular on the bench for the Serie A side and played 54 games in 2 years for the reserve team. In his third season, Verona assistant Marco Baroni, ex defender of the Scudetto winning Napoli side of Diego Maradona was signed as head coach of Carrarese Calcio and signed Vanstrattan immediately in the 2003–04 season, where he made his first team debut in Italy. However, in the first game of that season Vanstrattan suffered a serious knee injury rupturing his right knee ACL and missed the remainder of the season. In January 2004, his loan was ended and Vanstrattan returned to Verona where he signed a 4-year contract extension. In June 2004, the co-ownership deal was terminated and Verona received full registration rights.
Juventus
Vanstrattan was involved in a controversial transfer saga in the summer of 2007. After ending his contract with Verona by mutual agreement, Jess returned home to Australia in June, criticising Verona for several years of not fulfilling promises made. He signed for Juventus a month later. Vanstrattan played pre-season games for the Old Lady, becoming the first Australian to turn out for the club. However, in early August 2007, the Lega Calcio ruled that the goalkeeper's contract at Juventus was illegal after Verona falsified documents including the falsification of Vanstrattan's signature in an attempt to block the transfer of the player to Juventus and the transfer was to be cancelled until courts could decide an outcome. Vanstrattan needed to return to Verona officially under contract again, although only for four days, within which time the courts found Verona guilty. The club was ordered to agree on a loan deal which saw the player return to Juventus on 21 August, in time for the 2007–08 Serie A season. Vanstrattan played for Juventus in China, Hong Kong and Australia in friendly matches. In June 2008, Vanstrattan did not agree to a three-year contract extension with Juventus and was released by both Verona and Juve.
On 7 October 2008, Vanstrattan became the first signing for Gold Coast United after being released by Juventus in June. On 3 August 2009 he succumbed to an ankle injury sustained while training in preparation for the first game of the 2009–10 A-League season. He was sidelined for several weeks but recovered to play the rest of the season, and after a slow start was able to put in several man of the match performances.
Central Coast Mariners
On 19 July 2010, Vantstrattan was signed by the Central Coast Mariners after he wanted to move back home. Central Coast had recently lost first choice goal keeper Danny Vukovic to Turkish club Konyaspor. Unfortunately, 3 games after signing with the club, Vanstrattan suffered a second ACL rupture and missed the duration of the season. On 14 April 2011 Vanstrattan was released by the Mariners.
In 2014, Vanstrattan became the goalkeeping coach for Central Coast Mariners Academy. The academy was eventually dissolved in 2014. In 2015, Vanstrattan became the goalkeeping coach for Newcastle Jets
