Gray played all matches until round 14, before injuring his ankle at training, with his best performance being a 20 possession and 12 mark game against Hawthorn. He also impressed in Ports hefty Round 16 loss to Geelong after being moved into the midfield. He returned for two matches late in the 2008 season and played a pivotal role in Port Adelaide's surprise defeat of North Melbourne, by scoring 3 goals. Gray had an outstanding year for Port Adelaide, despite the club having a difficult year. He was Port's most valuable player according to an AFL poll, proving he is a fan favourite. He was also rated by the club's staff, who awarded him the 2009 most improved award, to go with his 4th placing in the John Cahill Medal. Gray kicked 30 goals in 2009, as well as 23 goal assists - top 6 in the AFL. He also received 6 Brownlow Medal votes, despite never polling previously. His standout performance of the year was against Hawthorn, where he kicked 4 goals in a tight win to the Power, earning 3 Brownlow votes for his efforts. In Round 6 2010, Gray won the Showdown Medal for a five-goal effort against Adelaide. He finished the 2011 season on 32 goals, making him the leading goalkicker, a goal ahead of Jay Schulz. In Round 4, 2012, Gray hyper extended his knee in the dying seconds of the game against Collingwood, requiring a knee reconstruction and missing the remainder of the season. At the start of 2013 Gray decided to change his number from 17 to 9. The number 9 was his junior number. He also wanted to start again after his knee reconstruction. Gray had his breakout season in 2014, averaging 25 possessions and six clearances a match, while also kicking 42 goals and leading the league in goal assists. He polled votes in 18 of 22 games to win the AFL Coaches' Association (AFLCA) Champion player award and was named in the 2014 All-Australian team, as well as winning his first John Cahill Medal. Gray backed up his break out 2014 campaign with another outstanding season in 2015. He averaged 26 disposals, almost 8 clearances and more than a goal a game. In one of his best games for 2015, he won his second Showdown Medal in the first Showdown against the Adelaide Crows. At season's end, he was selected in the All-Australian team for the second consecutive year as well as winning his second consecutive John Cahill Medal. In October 2017, Port Adelaide FC released the news that Gray had been diagnosed with testicular cancer after the end of their finals campaign.