Helmet #1 1934-1940 - Michigan Wing. This helmet is represented on that 1983 patch on the left side, and here's a picture with Dutch Clark wearing it in 1938.
Helmet #2 1941 - 1946 Spider Stripe. There is a spider stripe helmet on the patch with a small crest.
Helmet #3 1947. Smooth-shelled helmet. No discernible patterns that I can see - see the Bill Dudley photo. This helmet is not represented on the patch.