
Kenny signed his first professional contact with Hibernian in 1996 and moved to Rangers four years later. His club career has been adventurous, with spells at Wolves, Celtic, Derby County, a successful return to Rangers, Bursaspor in Turkey, and Cardiff City. Kenny made his Scotland debut on 25 April 2001 in a 1-1 friendly draw with Poland. He waited nearly two years for his second appearance, scoring against Iceland in a Euro 2004 qualifier. He has remained a constant Scotland presence, often as an ever-willing lone striker.
In 2005, Kenny scored in three consecutive internationals, against Austria, Italy and a double against Norway. He entered the International Roll of Honour in October 2010 after winning his 50th cap in a Euro 2012 qualifier against Czech Republic.