The Pensions Regulator (TPR) has fined Swindon Town Football Company £22,900 after it failed to put eligible workers into a pension scheme.
The regulator said Swindon Town - the League One football club owned and currently managed by former Norwich City footballer Lee Power - had "repeatedly failed to comply with its automatic enrolment duties".
It said STFC was issued with a compliance notice on 18 August 2014 directing it to automatically enrol staff and pay contributions but failed to comply by the deadline of 17 October 2014.
The regulator added there were several further delays in the employer complying with their duties - delays which resulted in TPR's intervention escalating from a focus on remedial action to one of enforcement action.
TPR executive director of automatic enrolment Charles Counsell said: "This case illustrates what can happen when an employer buries their head in the sand and disregards their duties.
"If things aren't going well, then talk to us; don't ignore us. Failing to comply on time will not save you money. Not only do you risk a fine, you will also have to make back- dated contributions."
The regulator has outlined full details of the case - including a timeline of events - in a section 89 regulatory intervention report.
The regulator said it hoped other employers would learn lessons from this action - urging businesses not to ignore their duties and ask for help if they needed it.
It added that "deliberate non-compliance would not be tolerated" and warned if employers have received a fine, they will still have to pay it even if they go on to become compliant.
Swindon Town Football Club declined to comment.