Football League Competition returned in August 1919 and City continued their mid table existence in the Second Division.

As they moved into the 1920s there emerged a thread, namely finance, that was to run throughout the remainder of the club's history with varying consequences. To survive, the directors had pursued a policy of selling their better players to meet the costs of running the club in an area of the country still dominated by Rugby League. Whilst the likes of Mercer, Gilhooley, Stevens, Lee and others were allowed to leave - often attracting substantial transfer fees for their times - one player who did emerge, and yet managed to stay with the Tigers for over 14 years, was George 'Geordie' Maddison. A brilliant goalkeeper, he was to establish the tradition of good keepers that has remained with the club to this day. Whilst they retained their Second Division status throughout the whole of the decade, they never finished higher than fifth. Their flirtation with success was brief, often restricted to the odd success in the cup and the occasional journey into the promotion zone. Each time they only flattered to deceive. The potential remained, but its fulfilment was never achieved.

The 1929/30 season was a classic example of the rollercoaster that is Hull City. Success in the FA Cup saw the club reach the semi-final for the first (and only) time in their history. Only after a replay did they finally succumb to Arsenal (the eventual winners). If this disappointment was not enough, more was to arrive in the shape of relegation for the first time in their brief history. The long cup run had taken its toll on the club and a combination of injuries and a closing programme of nine games in 28 days saw the Tigers finish in their lowest league position to date, with only Notts County below them. Relegation to the Third Division (North) was the only reward for their endeavours.

Whilst their relegation partners gained promotion at the first time of asking, the Tigers took a little longer to adjust to their new life in Division Three (North). It wasn't until the 1932/33 season that Manager Haydn Green steered the Tigers to promotion as Champions, having remained unbeaten at home. Their return to the Second Division was to last only three seasons. In 1935/36, having been decimated by injuries and forced to use 32 players, they finished bottom of the Division winning only five games out of a possible 42 and conceding 111 goals in the process. The Tigers therefore spent the remaining years before the Second World War in Division Three (North), coming close to promotion on each occasion.