Kenny started playing with the Breage and District Band at the age of 10 and his first taste of contesting was at the CBBA Contest in 1995.
After a brief spell at St. Ives Band under Chris Harris, Kenny joined Lanner and District Silver Band in 2004 under Stuart Chappell. During his time at Lanner, one of the highlights was when they came 2nd in the 1st Section areas and playing in the 1st Section National Finals, gaining promotion to the Championship Section.
In 2006 Kenny joined Camborne and got to play at the National Finals, playing Judges of the Secret Court.
2007 saw Kenny play with Kernow Concert Brass before joining St. Keverne in 2008 where he played at the Yeovil Entertainment Contest before taking some time out from playing for a few years, apart from a guest contest appearance with Gweek in 2011 at the CBBA Contest.
In 2013, Kenny came out of retirement with Hayle Band and later joined Roche Brass in August 2013.