Yes, it probably can be done, but it would probably require removing the tracks from the boat. You'd probably need a jig with a drill press or milling machine to drill the holes properly.
However, IMHO, you'd be far better off upgrading the genoa fairlead cars to line-controlled fairleads instead. That would give you unlimited adjustment of the fairlead positions, rather than the fixed ones... and it is probably far faster to do.
From a post by Don Guillette, author of the book Sail Trim Users Guide:
The most important jib sail trim control is the fairleads and here's why. There are 4 things sail trim controls are controlling and they are draft depth, draft position, twist and angle of attack. Do you know how many of the 4 elemts are controlled by the fairleads? ALL OF THEM and that is why the fairleads are the most important jib sail trim control.
Do you know how many sailors use the fairleads to adjust the jib - probably about 50%. The rest just set them and forget them. If you have a masthead rig and you don't use the fairleads to adjust your jib your boat will never perform to top efficency. For one specific point of sail and wind condition you'll be right on and wrong for all others, like the broken clock.
Garhauer makes a genoa car upgrade kit that is reasonably priced and works quite well. I installed them earlier this year on my boat. BTW, those two holes probably will only work in a fairly small percentage of the conditions you'll be using that sail under, as Don points out. Upgrading to and using line-controlled genoa fairleads makes a lot more sense than adding pin stop holes to the track.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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