- May 1, 1989
- May 2, 1989
- May 3, 1989
- May 4, 1989
- May 5, 1989
- May 6, 1989 (This strip is used on the page for October 9 of the Dayspring Peanuts A Year's Worth of Smiles and Blessings Desk Calendar)
- May 7, 1989
- May 8, 1989
- May 9, 1989
- May 10, 1989
- May 11, 1989
- May 12, 1989
- May 13, 1989
- May 14, 1989
- May 15, 1989
- May 16, 1989
- May 17, 1989
- May 18, 1989
- May 19, 1989
- May 20, 1989 (This strip is used on the page for July 24 of the Dayspring Peanuts A Year's Worth of Smiles and Blessings Desk Calendar)
- May 21, 1989
- May 22, 1989
- May 23, 1989 (The day that the episode "The Music and Heroes of America" from This Is America, Charlie Brown first aired)
- May 24, 1989 (This strip references the game show Jeopardy!)
- May 25, 1989
- May 26, 1989
- May 27, 1989 (Lucy does not appear again until July 3, 1989)
- May 28, 1989
- May 29, 1989 (Linus does not appear again until July 4, 1989)
- May 30, 1989
- May 31, 1989
| ← April 1989 | June 1989→ |