In the age of sail, square rigged ships could barely make headway upwind.
They could, at most, fill their sails at 67.5 degrees (6 points) off the wind. Perpendicular to the wind is 90 degrees.
So if the wind is coming from 12:00 on a clock dial, the ship could fill its sails pointing a little below 2:00
But the actual sailing performance is worse than that. Much worse.
Because as the ship is pointing at maybe 2:15, it is side slipping to leeward due to the force of the wind on its sails not being converted efficiently to forward motion. The age of sail ships did not have a large keel that extended below the hull.
In addition, tacking these ships was extremely difficult and one would lose ground in every tack.
If one reads contemporary accounts, the fear of a "lee shore" is common because the ships can't sail upwind effectively.
http://www.cnrs-scrn.org/northern_mariner/vol13/tnm_13_4_29-39.pdf
Side question: How many instances of independent invention of the sail are known?
Just a local example, but if, as is now commonly thought, the Homer's epics predate writing in Greek culture--and if they're a vaguely accurate account of actual events--then we know prehistoric Greeks had sailing ships.
We also know, from the story of Iphigenia, that (at least according to oral tradition) Greeks at the time of the Trojan War didn't know how to sail upwind.
While it is difficult to say if they used sails, as no physical remains have lasted from so long ago, there has been new evidence of seafaring hominids uncovered on the Greek island of Crete. This might not directly connect to your question about the advent and use of sailing into the wind, it does illustrate just how old seafaring is.
http://news.discovery.com/human/evolution/ancient-hominids-sailors-seas.htm>
TL:DR for article: recently found lithic remains (Stone tools) of (perhaps) Homo erectus have been dated to 128,000 BCE in Crete, in the same style of African handaxes from 780,000 BCE, showing that these individuals did sail from the north shore of Africa to Crete before the rise of Homo sapiens