Are there any airports that require arriving/departing flights to fly under an obstruction? Are there any airports with approaches and/or departures that require pilots to fly under an obstruction at some point (thus meaning that, for at least a short segment of the approach or departure, there is not only a minimum safe altitude, but also a maximum safe altitude)?

I can imagine a few situations where this might occur, such as for an airport at the bottom of a deep, steep-sided valley with powerlines or a bridge across the top of the valley, but I don't know if any airports like this actually exist.
It would not surprise me if someone, somewhere had done it, maybe even for good reasons (for example, possibly during the barnstorming era, one of the world wars, or perhaps on an Air America / POW rescue mission or similar) but thinking about an airport doing it as standard procedure brings to my mind phrases like "outrageously dangerous", "criminally irresponsible", and "out of your mind".

So I'm going to go with no, there aren't.