Here's the thing...unless you can devote considerable amount of time to tennis there is always a chance you will lose to good lobber/pusher.
I have seen it happen in open tournaments to good players or ex college player who don't play 6 hrs per day anymore. That's the truth.
Reason you don't see it at the pro level is because they have perfect timing practicing every day for hours. They will simply take it on the rise or out of the air. Something that even if you develop will quickly go away if you don't have time to maintain that level by hitting every day, a luxury most of us don't have.
One thing is that as an amateur you can chose not to play with him anymore and no harm done. Life is too short do deal with that.
If you guys are part of the league and have to play one advice i would give you is don't underestimate him because of his choice of strokes BUT take easy almost as a practice match and clear your afternoon schedule since you will be on the court for a while.
it is after you relax you will find way that you can beat him. Often this notion that he is beating u with inferior strokes puts too much pressure on you to go for winners and punish him for his "poor strokes" while the truth is at this level you are not equipped to do that consistently.