Charles Ellicott Commentary Deuteronomy 11:14

"that I will give the rain of your land in its season, the former rain and the latter rain, that thou mayest gather in thy grain, and thy new wine, and thine oil." — Deuteronomy 11:14 (ASV)

The first rain (after sowing), the latter rain (just before harvest). In the ninth month and the first month respectively. (See Ezra 10:9, Ezra 10:13, and Joel 2:23.)

That you may gather in. —Literally, and you shall gather in. Rashi reminds us that this may mean “you, and not your enemies.” “They that have gathered it shall eat it” (Isaiah 62:8–9).