For
Killabeez:
5 Ways Connor MacLeod and Matthew McCormick never met (and 1 that they did):
How they didn't meet:
1592 -- Matthew Stewart missed half the lines in Kyd's "The Spanish Tragedy" because he was trying to spot the other immortal in the crowd. It might have helped if he'd known that he was looking for the cheerful, not-really-inebriated Scot selling roasted nuts and listening to the merchants' gossip between acts.
1628 -- Connor MacLeod turned down an offer of three times what his cargo of flour, salted cod, linen, and gunpowder was worth: the terms specified delivery to La Rochelle, and Richelieu's men held it too securely to make the job worth the risk. (If they'd doubled their offer, though, Connor would have done it, and left the harbor terrified of ghost ships in the bargain. They'd have burnt him at the stake for the offer, though, so he left them to their lost battle.)
1815 -- In the smoke and confusion of New Orleans, the madness of a city held by a soldier and guarded by a pirate and a voodoo queen, Matthew McCormick melted away down a French Quarter alley that only the longtime residents knew: it was that or stay to see what immortal was moving with the British. Actually, Adrian Montague was moving *ahead* of the British, and had no wish to meet another of his kind when he'd just taken a ball of lead through the bones of his right wrist and hand.
1886 -- Matthew McCormick almost ignored the immortal presence to keep admiring the new statue at Staten Island. Almost. Instead, he escorted his new wife home again.
1922 -- Between the Great War, the Influenza epidemic that had followed on its heels, and the shock of the changes in the estate taxes, an Anglo-Irish family in Wicklow died out. No one noticed except their creditors, the auctioneers hired to get the best prices for the family memorabilia, and the two immortals interested in the auction. Connor MacLeod bought out the Georgian silver and the portrait of Father Darius; a withered, dried up stick of a mortal solicitor outbid a thin, nervy British nobleman for a bound collection of family letters. The solicitor declined, quite properly, to name his client.
How they really met:
1748, Philadelphia, Pennsylvania -- In the aftermath (and remains of chairs and tables) of a 'discussion' in a bar, Matthew Buchanan hauled Sunda Kastagir out, arresting him for inciting to riot, and hauled Connor MacLeod out as well, for aiding, abetting, and encouraging. Both of the 'criminals' were drunk enough to nearly walk Buchanan into walls, hitching posts, and less-than-respectable women still abroad at that hour. They were also arguing with him in English, Latin fit for graffiti in abandoned Roman outposts, still worse Gaelic, gutter Arabic (all of which Matthew understood), and an African languages Matthew hadn't heard in fifty years and hadn't understood then.
They were drunk enough that it took half an hour for them to realize that the rooms they were in weren't a jail, and that being handed fresh-baked muffins and mismatched cups of just-brewed tea probably meant it wasn't a very formal arrest.
This includes, by the way, one of the odder details I ever researched: how far back muffins are period. The answer seems to be at least the 10th century CE, and possibly the 9th...