The Oak course is 3,219 yards from the back tees and the natural setting that the holes are designed around enhances its beauty. Surrounded by many large mature oak trees, this course has many natural elevation changes, natural wetlands, and spectacular views. The Oak course was named in 1998 during expansion and contains the seven of the original holes of the old back 9 when the course was just 18 holes. Oak #1 has been lengthened to a 500-yard par 5 from the back tees and Oak #5 was converted from a par 4 into a 526-yard par 5. The Oak course is also home to the signature hole at Lakeside, the well-known 2nd hole which is a Par 3 that requires the player to carry their tee shot over a large water hazard to a green that slopes from the back to the front.

The Oak course has 3 par 5's and also has 3 challenging par 3's. Similar to the Maple course, the par 5's can reward players who hit good shots with good chances to make birdies. Perhaps the most recognizable par 5 is Oak #7 which is a hole that requires a great 2nd shot or a precise 3rd shot to an island green for a good chance at an eagle or birdie. Two of the par 3's on the Oak side are protected by natural wetlands and require the player to carry the hazard to reach the green.