Alexander The Great

[Shatnerfan]

Did Alexander ever fight the Romans?

[Clanad]

Although it's generally thought that the Roman Republic was established June 14, 510(BC) and was on the ascendancy by the time Alexander died at age 32 on June 13, 323(BC), their paths were divergent.  Following Alexander's death, his "Empire" collapsed rather quickly for want of a single strong leader. It was all soon added to the Roman empire but with the Greek civilizing and cultural influences dominating Rome for centuries to come. 

Actually, by birthright, Alexander was a Macedonian.  His father Phillip, made himself master of all of the Greeks following the disatrous war between the Sparta and Athens "city-states"... More than you probably wanted to know...

[Octavius]

Alexander the Great did not battle with the Romans.  He fought, the Greeks, Persians, Spartans, Indians, Thessalians and Thebans.

In 323 BC, on the sundown of 10th of June, after the ten day fever, in the Palace of Nabukodonossor, Alexander died.

In 146 BC, Macedonia and Greece became direct Roman provinces after a short-lived rebellion by the Macedonians, and in 64 BC, the Seleucid empire was conquered by the Roman general Pompey and became a Roman province.

AtG died in was revered by subsequent romans as a great leader of men and his tomb in Alexandria was visited by many prominent romans including Julius Caesar in 45 BC and Augustus in 30 BC. 

[Octavius]

It's worth pointing out - that his 'Greatness' refers to his military achievements and not his personality(!).

Inheriting a kingdom (Macedonia) from his father didn't really please Alexander. What kind of hero gets everything given to him? This wouldn't satisfy Achilles or Hercules and it wouldn't satisfy him. 

Alexander wanted to get started conquering ASAP.

He got his first opportunity almost immediately. Some of the Greek city-states saw the ascension of the 20-year-old Alexander as a chance to regain their independence from the foreign Macedonians.

Alexander took care of the little rebellion post-haste. To set an example, he completely razed the Greek city of Thebes in 335 B.C., killing most of the population -- including women and children (nice!) -- and enslaving those few left alive. After that the Greeks were happily united behind Alexander and he could focus his attention on expanding the empire.

He immediately began pushing east, against the old enemy Persia.  The rest, as they say,  is history....

[Yeah Bee]

No they were years apart, although a watched a documentary about two generals doing a fictive battle between a big roman leader and Big-Alex. And Alex acctually won

[Ray The Grey]

Footnote:

He bequeathed his empire to...."The strongest" person in his empire - very Darwinian.