Need help! Stitching

hello everyone. I am doing a sheath that has a welt, a wedge and a strap that wraps around the outside of the sheath. Where the strap wraps around I have six layes and of course the rest of the sheath taperes. My problem is getting my thread holes to to follow a groove ive placed in the back that matches the front. I want good clean stitching on both sides that line up in the back as well as the front. I used a drill press to drill my holes and tried to get the angle right. Can't believe how this would be done free hand.....how do i do this?
 
What I do Is first glue it all together put the grouve in the front, drill the holes and then grove the back following the holes then sew it all together. if you grove the back first it is real hadmaking sure the drilled holes line up with it so just grove it after.Hope this helps
 
Thanks Gahagan, I had thought of that but wanted to make sure there wasnt some technique out there i wasnt aware of. That makes sence to me.
 
The way that I do it is, get the front and back pieces as close a match in size as I can, then groove both pieces, then pre-punch the front piece, and glue it all up, then put it in the stiching pony, and using an awl, push through the front hole and into the back piece just enough to see the tip of the awl starting to stick through, if it is in the groove push it on through, if it is not in the groove, pull it out and adjust it untill it hits the groove. This has worked well for me, but it is a little slow if the front and back pieces are not sized well, and can be a little hard to push through on 4 layers of 10-11 oz. leather. I think I got this tip from a Chuck Burrows DVD on sheath making.
 
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The first picture is an overall view of my stitch puncning jig and the second is a close-up showing the needle chucked up unto the drill press. Niether picture shows it well, but there are two 1/4" holes in the board that is clamped to the table of the drill. The one in the middle of the board is for use when the work can be layed flat. The hole just inside the edge is for when the work will not lay flat on the board. The needle is just a drapery needle that I picked up at a local craft shop. It's just a bit larger in diameter than the stitching needle that I sew the leather with.

This jig is not used with the power on. The needle is not drilled into the leather. The levers are just used to push the needle through the leather. It works real good for keeping the holes straight from one side of the leather work to the other and within groves on both sides if the groves are made equal distance from the edge of the work. I got the idea from Tim Lively's video.

Doug Lester
 
The way that I do it is, get the front and back pieces as close a match in size as I can, then groove both pieces, then pre-punch the front piece, and glue it all up, then put it in the stiching pony, and using an awl, push through the front hole and into the back piece just enough to see the tip of the awl starting to stick through, if it is in the groove push it on through, if it is not in the groove, pull it out and adjust it untill it hits the groove. This has worked well for me, but it is a little slow if the front and back pieces are not sized well, and can be a little hard to push through on 4 layers of 10-11 oz. leather. I think I got this tip from a Chuck Burrows DVD on sheath making.

I kind of do the same but once the front holes are made and it's glued up I punch 2 holes one stitch apart and then run the same over stitch wheel over the back side that I used on the front. This way I have s spot to aim for on the back. I find it helps keep the stitches evenly spaced on the back.
 
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