- May 1, 1959
- May 2, 1959
- May 3, 1959
- May 4, 1959
- May 5, 1959
- May 6, 1959
- May 7, 1959
- May 8, 1959
- May 9, 1959
- May 10, 1959
- May 11, 1959
- May 12, 1959
- May 13, 1959
- May 14, 1959 (This strip is adapted in the episode "Reach for the Stars" from the 2014 French TV series Peanuts)
- May 15, 1959
- May 16, 1959
- May 17, 1959 (This strip is adapted in Good Grief, Charlie Brown: Peanuts)
- May 18, 1959
- May 19, 1959
- May 20, 1959
- May 21, 1959
- May 22, 1959
- May 23, 1959
- May 24, 1959
- May 25, 1959
- May 26, 1959 (Sally Brown is born. The character would remain unseen until August 23, 1959)
- May 27, 1959
- May 28, 1959
- May 29, 1959
- May 30, 1959 (This strip is adapted in a 1959 Ford commercial)
- May 31, 1959 (The segment "Kite" from The Charlie Brown and Snoopy Show episode "You Can't Win, Charlie Brown")
