Due to increasing lumber prices and declining raw material quality, secondary hardwood products manufacturers are placing heavy emphasis on lumber yield improvements in recent years. Cutting bill requirements are one of the parameters that directly influence lumber yield obtained in rough mills. Cutting bill requirements describe the parts to be produced from the incoming lumber in the rough mill in terms of geometry and quantity. By understanding the interaction of cutting bill requirements on lumber yield, strategies can be developed to create cutting bills whose requirements are such that maximum yield is achieved. Computer based rough mill simulation techniques and statistical methods were used to create a novel yield estimation model based on the method of least squares. The model classifies cutting bills according to their expected level of lumber yield and can thus be used to create cutting bills that result in maximum yield.