Each hole on a golf course is assigned a handicap that has both a technical meaning and a perception of difficulty. Handicap is based in large part on average scoring difference between strong and poor golfers, but it is not necessarily the same as “difficulty”. Handicapping is important to the game of golf, as it affects certain formats of tournament play. Hole difficulty is also important to players as they plan their shots. As a summer research project supported by the Northern Kentucky University UR-STEM program, we investigated factors that play into golf courses’ handicap rating for each hole. We also explored discrepancies between the scorecard handicap, observed handicap, and difficulty ratings. The analyses reveal interesting insight into the relationship between hole difficulty and players’ skill levels.