The case concerned the Forest Hill caravan park, in Wrotham, Kent, the owners of which had a history of felling trees covered by TPOs.
Planning permission for the park had been granted in 1983 and a TPO, protecting certain trees on the site, was issued soon thereafter.
Due to repeated breaches of the TPO, Tonbridge and Malling Borough Council launched enforcement proceedings.
And, in 2008, the owners of the park gave formal undertakings to a judge that the unlawful felling would cease.
Earlier this year, the park's current owners, Reuben and Royston Barney-Smith, applied to the High Court to be released from those undertakings.
That application was refused and now the Court of Appeal has dismissed the brothers' challenge to that decision.
The 1983 TPO forbade felling, uprooting or other forms of destruction of a number of trees on the site that were pinpointed on a map.
However, it stated that such felling would be permitted where "immediately required" for the implementation of the planning consent.
The permission did not limit the number of caravans on the site and the brothers argued that tree felling was necessary to expand the number of pitches, currently 33.
The brothers argued that the TPO made it impossible to "fully implement" the 1983 planning permission. But the judge, Sir Geoffrey Vos, ruled that this was "misconceived".
The judge noted the importance of the planning and tree preservation regimes working in harmony.
The planning permission permitted operations that were objectively required to permit the land's use as a caravan park, he said, and that use could continue without any more caravans being brought onto the site and without further felling of trees in order to do so.
Sir Vos said that, though the number of caravans was not limited by the planning permission, the brothers' personal, commercial, preferences in respect of the site's use were irrelevant.
The permission had been granted in the expectation of the subsequent TPO, which required that trees could only be felled according to its strict terms.
Properly understood, the planning permission and the TPO were perfectly compatible and there was never any question of the former nullifying or overriding the latter, the judge ruled.