Following their F.A. Cup exploits the previous season, the 1925/26 season turned out to be the Club's most disappointing since joining the Southern League. Yeovil finished in a mid-table position in their Section and in the F.A. Cup, although exempted until the 4th qualifying round for the first time, lost 3-1 at Torquay to fall at the first hurdle.

A quote in the Yeovil programme for 5th December, 1925, states: "Barracking still appears to be the 'forte' of the ignorant, in an effort to cure the evil, Notts County have gone to the expense of engaging detectives to weed the nuisances out"

The 1926/27 season was yet another disappointing one, Yeovil slumping to twelfth in the Western Section of the Southern League, which was won by Torquay United. In the F.A. Cup it was back to the Preliminary Round again.

Results: Preliminary Round - Yeovil 10 Street 1, 1st Round Qual. - Yeovil 3 Bristol St George 0, 2nd Qual. - Yeovil 5 St Weymouth Austell 0, 3rd Qual. - Yeovil 3 Barry 1, 4th Qual. - Weymouth 4 Yeovil 1.

For the first match at Weymouth, The Great Western Railway Company ran an excursion with 600 fans paying 2/6d. each. The game, however, was called off only minutes before half-time as the ground was waterlogged.

The 18th September, 1926, saw Johnny Hayward score his 500th goal for the club, a feat no other player is ever likely to achieve. On a more serious note, the programme of 27th November reported: "for the benefit of those readers who are not already aware of the fact, W. H. Poole has been given notice to terminate his engagement with the Club. We regret the necessity of this step, but when a man is not amenable to discipline it is to the interest of the Club (no matter how good a player he may be) that they part company and this is the course adopted by the Directors."

On Boxing Day, Yeovil's number 4, Ernie Hyman, sustained internal injuries and on the following Friday died in the Yeovil & District Hospital at the age of 22. A fund was set up which amounted to £80 6s. Od. which was invested in War Stock. During the season, the Queen Street end terracing was covered for the first time.

At the end of this season, the Club made its first ever application to join the Third Division of the Football league. A report at the time states: "A big effort is to be made to gain admission to the English League (Div.III). The meeting at the Town Hall on Tuesday, 26th April, 1927 was most successful and the motion that the application be made was carried with enthusiasm. For the Directors to be able to carry forward the project is entirely due to the work during the past few weeks of the Shareholders' Committee, who have worked untiringly. The satisfactory report they were able to put forward was most encouraging and with still further promises of financial support going forward. From information to hand we are able to state that the Club is hopeful of being successful in their application. Yeovil has for many years been one of the principal association football districts in the West of England and should this important step be confirmed and Yeovil & Petters next season figure in English League football, then this will have mainly been brought about by the work of the Committee of which Mr. C.E.R. Dye has been such an enthusiastic Chairman and Mr. Stanley Vincent an indefatigable secretary. Both these gentleman and their fellow workers have spared no effort to bring about achievement of the object in view and they are to be commended for what they have done."