The 1949-50 campaign was Lynn's second season with paid players and the list of summer signings looked impressive. Goalkeeper Percy Hooper arrived having been with Tottenham Hotspur from 1935-1947. Cecil Heydon had experience with Derby, Doncaster and Rochdale, Walter Price ex-Tranmere (10 years) and Rochdale, Sidney High (Luton and Watford); John Williams, Cardiff (8 seasons) and Northampton (4 seasons); Cliff Whitelum(Sunderland 1939-47 and Sheffield United); Harry Cranfield (Fulham, Bristol Rovers, Colchester United).
Joining the club on trial was Richard Everett formerly of Darlington and Worksop.
By the beginning of October, Lynn had won all nine games with Dick Everett scoring 12 times. At the end of his trial period he needed somewhere to live. In stepped the Supporters' Club and a couple of local supporters providing the means to purchase a second house whilst a fairly large house in the country had become available which could be adapted to house two married players.
Work began on a second section of the shelter on the Broad Walk side of the ground with plans for the provision of a second refreshment kiosk which would be staffed by the Supporter's Club.
For the first time the responsibility of selecting the team was that of the coach, Ken Gadsby, and not a selection committee.
November 1949 saw the installation of two floodlights to be used for training. The first time they were used causing such a glow in the night sky that many thought it was a fire and the fire service was sent to check.
The rules of the Norfolk Senior Cup presented Lynn with a problem. A maximum of five professionals was allowed and Lynn had a choice of fielding a weakened first team or entering the Reserves. Fearing a fixture backlog if the first team was used, Lynn Reserves entered the competition and they did quite well defeating Wroxham in front of 3,695 and then Thorpe Village, at the third attempt, before losing to CNSOBU in a replay.
Lynn made progress in the FA Cup, defeating March, Histon Institute and Cambridge Town before appearing in front of a Walks crowd of 9,738 that saw Lynn draw against Dartford in the 4th qualifying round. They went on to win the replay and appear in the first round proper, the first time since the 1937-38 season.
Norman Rowe was Lynn's full back and, in some matches, the only Norfolk born player in the Lynn team. He had refused the opportunity of being paid but was spotted playing for Lynn in the FA Cup 1st Round Proper match against Nuneaton by a scout from Derby County and, after a trial, he signed for Derby in December 1949 and made his Baseball Ground debut against Chelsea the following May. Rowe moved on to Walsall in 1952 making 26 appearances before returning to Lynn in July 1953.
Prior to the Nuneaton game Lynn had been undefeated in all competitions.
February saw the visit of Yarmouth Town for a league fixture and with them came “Little Audrey” a performing seal. The month also saw the Supporters' Club donate a further £100 to the club which was to be put towards the housing fund. It brought the total donated to the club that season to £850.
At the beginning of March it looked as if Lynn had a chance of winning the Eastern Counties League but a run of bad form meant that they could not turn their games in hand into points. Lynn finished runners-up to Spurs A.
Ken Gadsby's contract as player coach was coming to an end. The club offered a year's contract but Gadsby wanted three – it became stalemate. An extra-ordinary meeting of the club was called by its members to discuss the matter – the majority felt that the Committee was right and Ken Gadsby left – joining March Town. He scored in Lynn's final game of the season as did Cliff Whitelum. The two goals by Whitelum saw him reach the fifty mark from forty-eight appearances.
Lynn's only silverware of the season was the Miller Shield (6-2 against Gorleston watched by 5,714) and the Lynn Charity Cup (5-1 against Histon Institute - attendance 4,717).
Lynn decided to increase the number of professional players and with that in mind applied to enter the Reserves' team in the United Counties League for the next season, an application that was rejected.