| SEPTEMBERSONG | It's a long, long time from May to December in this Kurt Weill/Maxwell Anderson number (9,4) |
| SEPTEMBER | It's a long, long time from May to this sapphire birthstone month |
| EVERGREENTREES | You can see lots of them in December (In this clue's answer, note letters 8-13) |
| ABILENE | City in Kansas of which Wild Bill Hickok was marshal from April to December in 1871 |
| REACH | "Oh, it's a long, long while, from May to December; But the days grow short, when you ... September" |
| YEARLONG | January to December in 1975 dragged out (8) |
| MILANMELINDO | IBF Junior Flyweight champion from May to December 2017 |
| DECEMBER | "Oh, it's a long, long while, from May to ...; But the days grow short, when you reach September" |
| PRIMEMINISTER | What Johnson is May to July? (5,8) |
| TODECEMBER | "Oh, it's a long, long while from May ...; But the days grow short when you reach September" (2,8) |
| KIDNAPPED | Novel by Robert Louis Stevenson first published in the magazine Young Folks from May to July 1886 |
| ANTONRODGERS | Actor who starred in BBC TV sitcom May to December from 1989-94 (5,7) |
| INDY | ___ 500 (annual auto race postponed from May to August this year) |
| WHITE | Frances _, May to December star who voices Granny Pig in Peppa Pig (5) |
| STEERAGE | Direct a ship's course for a long time from the lower decks (8) |
| ALEXARTHUR | WBO Super Featherweight champion from May to September 2008 (4,6) |
| MIGHTY | Stout from May to end of July (6) |
| INSEASON | Like watermelons from May to September |
| GEMINI | Star sign that runs from May to June (6) |
| WGA | Org. that was on strike from May to September |
