The season opened with an unbeaten run of 5 matches in the League, with Ken McDonald repeating his opening day performance from the previous season by scoring. It augured well for the prospects of a young team, under the guidance of their legendary captain and seemingly permanent fixture at left-back: Matt Bell.
That sequence of League results would not be bettered all season, but at the time they weren't to know that and they settled down to be a solid rather than a spectacular outfit for the remaining months of 1929 - never straying far from mid-table. When January 1930 arrived, there was the FA Cup to provide added interest to a Tiger season that was starting to stagnate; how wrong that impression would prove to be.
"I think the Tigers will go a long way in the Cup this year," said club captain Matt Bell prior to the Tigers 3rd round tie, away to Plymouth Argyle. Whether it was a prophetic assessment of the club's chances, or just a practical observation about the longest journey, in the club's cup ventures thus far, only time would tell.
Whatever prompted his statement, a 4-3 victory over the Division 3S side - a hat-trick from Stan Alexander and a single goal from Dally Duncan - ensured the Tigers overcame a strong Argyle fight back and also guaranteed their involvement in the Cup for at least one more round.
Their next opponents were Blackpool, who were strongly contesting promotion from Division Two. Even though the Tigers had inflicted on the 'Tangerines' their first home defeat of the season some two months earlier, and were enjoying home advantage in this first ever meeting between the two teams, a stern examination of the Tigers capabilities was expected.
The test was stern enough but the Tigers resolve more than matched it and they finished the game as victors (3-1) with goals from Alexander, Starling and Mills. The draw for Round 5 however gave them an even sterner test - away to Manchester City.
Riding high in Division One, the Maine Road outfit were expected to have little trouble in disposing of the Tigers, whose task was made even more difficult when Matt Bell was forced to withdraw from the team, through injury. His role as captain and left-back was taken by Jim Howieson, whose normal position was as an inside-left.
An early goal by Man City's winger, Toseland, did nothing to suggest to the 58,000 crowd that an upset was on the cards, but when Mills equalised Howieson marshalled the Tigers superbly. Alexander didn't maintain his record of scoring in every round, but it was from his pass that City's Bill Taylor ran through the home defence to score the deciding goal, thus giving the Tigers a surprise but thoroughly deserved 2-1 victory.
The draw for the quarter finals saw the Tigers again on their travels, and again it involved a trip to a higher division team: Newcastle United. A doughty cup side - they had previously won the trophy twice - they were strongly fancied for the cup, even though their league season was not pulling up any trees.
A crowd of 63, 486 saw the Magpies take a 27th minute lead through a Tom Lang header, but Stan Alexander silenced them with an equaliser that concluded the afternoon's scoring. When the Geordies visited Anlaby Road, a crowd of 32,930 saw the Tigers gain a 1-0 victory in a dour struggle.
The goal came direct from the kick-off for the second half and, in a masterly display of inter passing, not a single Newcastle player touched the ball from the restart until their goalkeeper, Albert McInroy, picked it out of the back of the net. The Tigers were through to the semi-finals.
They were paired against Arsenal, the venue for this encounter being Elland Road, Leeds. Whilst Arsenal contained the stars - including Davy Jack, the first footballer to command a transfer fee of £10,000 - it was the Tigers who took the lead, when after 15 minutes, Jim Howieson lobbed the Gunners keeper from just inside the Arsenal half.
On the half hour mark the Tigers doubled their lead as 'Dally' Duncan shot home, the ball taking a deflection off Arsenal's Eddie Hapgood on its way to the net. A major shock was on the cards as the Tigers reached half-time two goals to the good.
In a bruising second half the Gunners approach was to make it more of a physical, rather than a passing, contest and in the 67th minute pulled a goal back via Jack. Eight minutes from time Arsenal equalised through Cliff Bastin as the Tigers team, severely hampered by injuries to Walsh and Mills, failed to hang on.
The replay was held at Villa Park and the Tigers were minus Walsh and Alexander - through injury - from the team that had caused such panic in the previous meeting. Their task was made no easier when centre-half Arthur Childs was controversially sent off early in the second half. By this time the Tigers were already trailing to an 11th minute goal from Davy Jack. It proved to be the only goal of the game and the Tigers' cup dream was over.
If the dream had ended, the nightmare was just beginning. A combination of injuries and a heavy programme of rearranged games saw the Tigers drop down the League; by the end of the season they found themselves in one of the relegation places. For their efforts in the Cup, the only reward was to face Division 3N football the following season.
At the start of season 1929/30, the Tigers had never played in the top flight division, they'd never played at Wembley and they'd never played in a Division of the League lower than the Second. At the end of it one of those records was gone. It was the wrong one.