Carey missed five games early in 1999 AFL season through injury, and spent much of the year in the forward line closer to goals. He averaged a career high 3.8 goals per game for the season, to go with 7 marks and 18 disposals. He helped North to a 15 and 2 record after his return from injury, in another List of Australian Football League premiers year for the Kangaroos. In round 8, Careys first game back from injury, he kicked 7 goals against Hawthorn Football Club. Once again Careys late season form was unparalleled, and in the nine games leading up to the 1999 AFL Grand Final he averaged 8 marks, 19 disposals and 5.1 goals per game. He kicked 9 goals against Geelong Football Club in Round 16, followed it up the next week with a 10-goal, 12 mark and 24 disposal performance in a losing side against Essendon Football Club and in the wet in a qualifying final against Port Adelaide Football Club had 11 marks, 24 disposals and 6 goals in one of his greatest finals performances. Matched up against Carltons Stephen Silvagni in the grand final, Carey played a slightly unfamiliar role. After marking and kicking North Melbournes opening goal in the first quarter, he struggled to get on top of the Carlton champion and was moved to the midfield after half time. He then gathered the most disposals afield in the third quarter and was the catalyst in a dominant quarter for North, before returning to the forward line in the final term to take a spectacular one handed mark and kick the final goal of the game.. How many more goals did Carey kick against Essendon Football Club than he kicked against Port Adelaide?