Bill Yeadon, the brother of the NAHC President and like his brother, a legendary player, was also the owner, General Manager and coach of the New York Eagles. While nearly everyone in the hockey community had nothing but the utmost respect for Bill, his team's finances were a mess. A mess partially due to the exorbitant rent the team paid the Bigsby Management Company, which owned and operated the Bigsby Gardens and the Eagles' main rival, the New York Shamrocks. The franchise had been saved several years ago when Detroit owner John Connolly Jr had purchased the club's debt in return for the right to swap rosters. But the Eagles' struggles continued and things came to another crucial juncture in 1939. And this time, it seemed there was no one to rescue the squad.

The Eagles' final season in New York was a poor one - they won just eight games and garnered just 26 points, though they did allow fewer goals than the Montreal Valiants, and scored one more than Montreal as well. Montreal finished five points ahead of the Eagles. The top of the standings was a near-perfect match to those of the previous season with the Bees winning the regular season title with a 33-7-8, 74-point season. Detroit was second (again) and Toronto third (ditto) though the Shamrocks leaped over the Chicago Packers into fourth.

The demise of the Montreal Nationals left the NAHC with seven clubs. That what had been the class of the league just a few short years ago was now gone was a tough pill for many to swallow. That the club had been bought, lock, stock and barrel by the New York Shamrocks' owner Sam Bigsby, then cannibalized to support his club was an even more bitter pill. Still, the league soldiered on, and that phrase would take on a whole new meeting just a few months after the Challenge Cup Finals ended when Canada went to war with the German Reich alongside the rest of the British Commonwealth nations.

On the ice the Boston Bees had now firmly stepped into the role of best team in the league. They put up a 34-13-1 mark and their 69 points were seven ahead of the runner-up Detroit Olympians, who themselves barely edged out third-place Toronto. There was a definite divide thereafter, with the top three firmly and obviously superior to the other four clubs. Of those "second division" squads, the Chicago Packers and New York Shamrocks were respectable while the New York Eagles and Montreal Valiants (surprisingly in the latter's case) were terrible.