I have done a bit with hand cranks. The 99s need to have a screw taken out or modify the bracket to wind the bobbin with any spoked hand wheel. The screw out is the option I use - no harm done.
The Singer 15s or 27s that have been converted to electric and are as found using a 'new' 'conversion' bobbin winder with the conversion hand wheel will not likely work with a spoked hand wheel at all - the bobbin winder tire extends past the part of the wheel it should ride on and into the spokes. I don't know of any bobbin winders you can put on them and will work. Plus many of the real old machine do not have that mounting for the HC attachment. I have two 27s that were converted to electric. The Singer badge was removed and the mounting block for the bobbin winder was ground off. Then there was a replacement bobbin winder installed on the top of the machine at the belt guard hole. These do not convert back to the spoked wheel and still wind a bobbin whether a 27 or a 15-30 conversion.
Back to the question of winding a bobbin on a 99 - yes it will wind on the 99 with a spoked wheel. In the picture, the screw driver is resting on that bracket. The screw that holds the bracket can be removed or modify the bracket to allow the bobbin winder to reach the wheel.
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Last edited by miriam; 05-19-2014 at 02:35 AM.