Yes, highly unlikely, but not impossible and it has happened before. For the person changing their own oil at a leisurely pace, it's very unlikely. For mechanic changing oil on multiple cars for a living, or a fleet mechanic servicing an entire fleet, it invites the potential for mistakes.
In professional situations where a pump is used, it's also more risky. The end of the nozzle could be dirty, or could've picked up junk from another persons fill hole etc.