After failing to agree re-signing terms, he joined Belfast club Distillery at the start of the 1911–12 season, helping to win the Gold Cup and the CAS despite a long-term injury interrupting his playing career,[2] and becoming the first Englishman to captain an Irish Football League representative team.
[4] He made his debut at home against Barnsley in September 1919 and, having taken over the captaincy from Billy Cope for the 1922–23 season, led the West Ham side that gained promotion to the First Division and reached the FA Cup Final against his former club, Bolton Wanderers, in 1923.
In an effort to rebuild the club's fortunes and help them survive during these difficult times financially, Kay created Saints' first nursery side, and before long a new generation of young players came into the first team having come through the nursery ranks, including Ted Drake (who later joined Arsenal and played for England) and Charlie Sillett (father of John and Peter), thus ushering in a new era for the club.
Led by Ted Drake, the team improved slightly on the previous season, winning a club record 15 out of 21 home matches, but only registering three away victories.
The most significant events of the season involved Ted Drake, who scored a hat trick in the opening day's match against Bradford City, was sent off against Grimsby Town in December and, inevitably, was sold for a record fee of £6,000 to Arsenal in March.
In the summer of 1934, Kay signed Laurie Fishlock from Millwall as a winger and promoted Norman Cole from the reserves, but the side lacked any real firepower.
The depressing form continued until Christmas, when the team won three consecutive matches, including their first away victory (against Swansea Town) ending a run of 33 away games without a win.
Predictably, the directors responded by selling their better players, with goalkeeper Billy Light (another product of the nursery side) being sold to West Bromwich Albion for £2,000.
At Southampton, severe financial problems and the continual sale of the club's best players, prevented Kay from realising his full potential as a manager.
He was, however, experienced, well respected and knowledgeable and not afraid to try out new ideas, and the combination of these qualities brought him to Liverpool's attention when it was clear that George Patterson would be unable to continue the managerial side of his role.
Despite the set-back of an opening day 1–6 defeat at Chelsea's Stamford Bridge, Liverpool finished the 1937–38 season comfortably in mid-table, with Alf Hanson top scorer on 14 league goals.
In the following season, Liverpool again finished in 11th position in the table, with Berry Nieuwenhuys, Willie Fagan and Phil Taylor joint top scorers in the league with 14 goals each.
In readiness for the next season, Kay snapped up young defender Bob Paisley on a free transfer from Bishop Auckland, as well as another future Liverpool legend Billy Liddell, but all their careers were then interrupted by the outbreak of World War II.
As the season reached its climax, several clubs were still in contention and on 31 May 1947 Liverpool went to Molineux to meet the leaders, Wolverhampton Wanderers needing to win to take the championship, as well as other results going in their favour.
They continued to be prolific scorers during Kay's period in charge but the club was unable to come close to another championship, finishing each of the next three seasons in the lower part of the top half of the table.