The words whiny, winy sound the same but have different meanings and spellings. Why do whiny, winy sound the same even though they are completely different words?
The answer is simple: whiny, winy are homophones of the English language.
whining; tending to whine or complain.
Having the qualities or taste of wine; heady or intoxicating.
Definitions from Wiktionary, Creative Commons Attribution/Share-Alike License, from The American Heritage® Dictionary of the English Language, 4th Edition and Wordnik.
Homophones (literally "same sound") are usually defined as words that share the same pronunciation, regardless of how they are spelled.