The FLYC utilizes US Sailing's Portsmouth Yardstick (PY) as a basis for handicapping racing competitors. The PY system is essentially a time-on-time rating system that assigns a multiplier to each boat that will convert her elapsed time to a corrected elapsed time. This allows boats of differing design and capability to compete against one another with the multiplier helping to level the playing field.

In addition to Portsmouth, the FLYC utilizes an additional "golf handicap" to further negate any remaining discrepancies between boats and competitors. This adjustment (sometimes referred to as a "Moss Factor") is calculated based on the relative difference of corrected finish times between an individual boat and the fleet average. After over a decade of use of this adjustment, the FLYC has seen very favorable results in terms of the enthusiasm