Barry was born in Suffolk, England in 1942. Joined Chelsea Football Club in 1957 as a young goalkeeper.
On 4 February 1957 he played for England Youth in a 2-2 draw against Yugoslavia at Stamford Bridge. On 4 March 1958 he was in goal as England Youth defeated Austria 3-2 at Highbury in London.
In the 1959-1960 season Chelsea won the F.A. Youth Cup. Barry was the back-up goalkeeper for future Chelsea and England star Peter Bonetti.
On Monday 14th March 1960 Barry played for Chelsea in a friendly against Boston United. A couple of goals from Chelsea legend Barry Bridges secured a 4-1 win.
The 5’9″ and 160 lbs goalkeeper spent his whole career at Chelsea as a reserve goalkeeper. Given a free transfer after the 1960-1961 season.
In April 1961 he recieved an offer to go to Canada and play for Toronto City in the newly-formed Eastern Canada Professional Soccer League. On Wednesday 26 April he signed for Toronto City.
On Thursday 11 May 1961 he arrived in Toronto together with eight other British imports, including Stan Matthews.
The opening game in Toronto was played on Saturday night May 20, with Toronto Italia beating Toronto City 3-2. 16,509 fans watched the game at Varsity Stadium. Barry was City’s goalkeeper that day.
He spent the 1961 ECPSL season mostly as an understudy to former Scottish International goalkeeper Tommy Younger. During the summer of 1961 Toronto also played in several exhibition games in Canada. This included games against the B.C. All-Stars and Real Madrid.
Toronto City won the regular season league championship based on goal average over Montreal Cantalia.
Barry returned to England after the 1961 ECPSL season.