Besides playing for his school Ndelela Primary, Chileshe joined Kalala Amateur Football Club in 1969 at the age of twelve.
He made his international debut on 26 March 1977 at the age of 19 in a friendly against Malawi which Zambia won 8–1 and he did enough to convince fans that a talented goalkeeper had arrived on the scene.
Nicknamed "The Black Cat" he won the Zambian FA cup when Roan beat Mufulira Wanderers 3 – 2 in a thrilling final played at Independence Stadium and was in Zambia's team at the CECAFA tournament later that year.
Chileshe was however backed by national team captain Ackim Musenge who said he deserved the award, rather than picking on old timers all the time.
"[1] The young goalkeeper was in goal at CAN 1978 in Ghana where Zambia were eliminated after a defeat, a win and a draw against the hosts, Upper Volta and Nigeria respectively.
He was then recalled to the national team and was one of the reserve goalkeepers when Zambia emerged victorious at CECAFA 1984 and he described it as a very emotional moment because he had participated in 4 previous tournaments and they had always failed to finish first.
In 1990, Chileshe decided to go to Swaziland where he coached various teams in a period of 5 years: Police Leopards, Manzini Wanderers and Mbabane Swallows.
Chileshe was in Swaziland until 2002 when his contract expired and is currently coaching FAZ Division II side Young Green Eagles in Kafue.