I know a little about 2 subjects. This is one. I'm a landscape architect and two easy examples of how to fix your problem came to mind. BTW...nice drawing.
I HIGHLY RECOMMEND YOU DO THIS...simply get some diamond tip masonry drill bits and drill some holes into your retaining wall about an inch above the ground. Also do the same from the other side of your wall at different levels in your wall, but that's below the ground surface that your retaining.
Doing this is not optional if you want your wall to last through the next rainfall in your area. This is to allow water from any sudden downpours as well as water trapped below the surface to escape, while leaving your yard in place.
The other option that's easily done is called a French drain. This is the most aesthetically pleasing way to move water because the entire drain is buried and cannot be seen. Easily done with the right equipment (varies widely from a mini excavator to a pick and shovel) or neighborhood kid to dig the trench for your pipe to lay in.
The opening to the drain would be where the question mark is on your drawing. And you would have the pipe traveling down the hill and UNDER where your retaining wall will be. Just 3" below the surface of the ground where your wall will be is sufficient to keep it from being pinched or crushed.
Make sure you level out the ground where the first layer of bricks that make up the base of your wall, and bury your pipe 3 inches below that. Cover with dirt. The only things you HAVE TO BE SURE OF is that your pipe must be laid in a straight line, and ALWAYS keep the fall. Meaning don't allow a hump of dirt make your pipe lift more than 1/8 inch or water and sediment will gather there, eventually clogging the drain. It only needs to be as long as about 6 inches at the least past your wall. But you can run it as far as you want. No one will even know its there. You can purchase everything you need at Walmart or your local home improvement store for cheap.
Oh yeah, avoid drilling any holes in the actual mortar/cement you use to hold the bricks in place to prevent weakening the structure. The amount of holes you need depend on the amount of water that comes your direction from other places around you. A 1" hole every 2 to 5 feet above the ground. With smaller holes placed closer together below the surface on other side of wall.