[1] Awarded his professional contract in February 1953,[2] Kennedy played alongside the likes of Duncan Edwards, Eddie Colman, David Pegg and Liam Whelan in United's FA Youth Cup winning side of 1953, when they defeated Wolverhampton Wanderers, 9–3 on aggregate.
Kennedy spent three seasons at Ewood Park, where his path to the first-team was blocked by long-serving England international Bill Eckersley.
[citation needed] On joining the "Saints", he was immediately drafted into the first-team, making his debut in the opening game of the 1959–60 season, a 2–2 draw with Norwich City.
[4] He retained his place for the next match, a 2–3 defeat at Chesterfield, before being replaced at left-back by fellow-Irishman Tommy Traynor, who kept the number 3 shirt for the rest of the season, at the end of which Southampton were Division 3 champions.
Kennedy only made four appearances for the Southampton reserves, with David Scurr blocking his way into the side,[5] and was given a free transfer at the end of the season.