|Debut:||01-Dec-40, League, (A) v. Bray Unknowns|
Harry’s form with B & I in the Leinster League brought him to the attention of the Dundalk Committee, particularly after he had scored 4 goals against the Dundalk Reserves team in the Metropolitan Cup during the 1939-40 season, and he was added to the Oriel Park panel for the following season.
Poor early season form, particularly away from home, left the team at the wrong end of the Shield. But there was a dramatic improvement following the promotion of Harry from the reserves at the beginning of the League, coupled with the signing of Paddy Barlow. Harry's promotion came after he scored six goals with the reserves in a 3-match run.
They both made their Oriel Park debuts on December 8th 1940 against St James’s Gate, who had just finished as runaway winners of the Shield, dropping just a single point from 10 games. In an early Christmas present for the 1600 crowd Harry supplied two goals, and Paddy got the third, in a surprise 3-2 home win.
This was the start of a home sequence never previously seen by Dundalk supporters. Prior to the game against the Gate there had been just three wins from seven home games, which yielded ten home goals. Over the next eleven weeks until the end of February Dundalk won all seven home games, and knocked in 32 goals. Harry Bryan scored in every game, hitting five doubles into the bargain.
The run included a first round FAI Cup match against St James’s Gate when a record crowd of 4,800 saw a stunning 5-1 win—Harry got his by-now usual pair, as did Paddy Barlow—which earned a second round 3-match marathon with Shelbourne. This was finally settled by goals from Harry and Charlie Reid.
While Cork United proved too strong in the semi-final, Harry’s two-month goal burst had propelled him to the top of the goal scorer’s list for the season. From his final tally of 16 goals from 20 appearances 12 had come in that magic spell.
The proceeds from the 1941 Cup run provided the financial muscle to acquire virtually a new team for the following season that led to Cup glory.
With Artie Kelly recruited for the centre-forward spot, Harry’s first team chances were limited in his second season but when called upon he still managed to get his name on the score sheet, finishing with a very respectable 2-season record of 19 goals from 27 starts.
Afterwards he went back to his local club at Clontarf where he later struck up a highly productive partnership with the teen age Paddy Ambrose, before Paddy’s move to Shamrock Rovers and fame.