When you originally posted, I made some recommendations of thigs to check. Unless it's down/lodged or stringy wire grass, you should be able to cut just dandy. We now use a newer Deere sickle for all our hay, but up until about 8 or 9 years ago we used a pair if IH pitman mowers for all our hay. Not as fast as the Deere one, but in normal conditions you could go along at 5 or 6 MPH just fine. We rarely sharpened ours near the end: You could buy an aftermarket under-serrated knife from AI for about $120. We'd cut all our hay (about 70 acres - only one cut per year) for about 3 or 4 years, then get a new knife. Occasionally you'd damage a section on something, and when you had the knife out to repair it you might touch up a few of the worst sections, but overall the new knives worked superb for long periods without service.
Biggest thing to check: Is your knife in register? If not registered correctly, it won't cut worth a dang no matter what. Lots of people overlook this, and I suspect it's one of the chief reasons you see so many sickle mowers parked in the weeds or in fence bottoms. Apart from this: Are the hold-downs keeping knife close to the ledgers? Is the knife angle set right (level or angled down into the crop just slightly)? Are you making sure you're not trying to move the bar through grass that's already cut?
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