In 2007 and 2008 after several seasons missing only a handful of games, Kennelly suffered a series of serious leg and shoulder injuries which became major setbacks to his AFL career. His knee buckled from a heavy tackle from the Melbourne Demons' Byron Pickett, causing an anterior cruciate ligament tear and seeing him miss several matches and later matches due to complications. In 2008, he again injured his knee, dislocating his knee cap and injuring his shoulder. He was selected in the Dream Team for the AFL Hall of Fame Tribute Match, but later withdrew due to injury. He was quick to recover, however, and made an appearance for the Swans the following week, though again succumbed to the injury curse. During the rest of 2008, Kennelly's shoulder continually dislocated during games and his unorthodox methods of popping it back in was the subject of much media interest.