War breaks out across Europe and MacLeod fights for the British against Napoleon. He unexpectedly meets Xavier St Cloud, along with his student, Morgan d'Estaing, as the British advance on Paris, ("Double Jeopardy"). Between the wars, he spends time in Switzerland with Brian Cullen, ("Courage"). War breaks out again and, during the last battles of the Napoleonic Wars, he meets his greatest teacher, Darius, on a battlefield, ("The Gathering"). Tired of war, but unable to live with Darius' teachings, he decides to leave Europe, but this time heads west, for the New World.

Travelling as far west as Montana, he sees John Durgan kill a priest for a gold crucifix, ("The Cross Of St Antoine"), but is unable to catch him. He spends sometime in Philadelphia around 1825, befriending David Keogh, ("Obsession"), before returning to Europe. After a visit to Peru in 1830, where he meets Gavriel Larca, ("Little Tin God"), he is reunited with Connor in London around 1832, but his romantic leanings almost cost him his head when bounty hunter Regan Cole first snares him and then frees him, ("Deadly Exposure"). After a brief encounter with Willie Kingsley, ("Diplomatic Immunity"), he leaves England and moves to Paris, where his attempts to set up a long term investment are frustrated by Nicholas Ward, ("The Vampire"), and he renews his friendship with Grace Chandel, who introduces him to Carlo Sendaro, ("Saving Grace"). He sets aside "European civilization" for a while during these years, travelling with gypsies during 1847, initially in the company of Jacob and Irena Galati, ("One Minute To Midnight"), but is cast out when the gypsies become convinced that he will never marry, ("The Darkness"). He travels to Spain, studying flamenco dancing and Spanish swordfighting with Otavio Consone during 1851, ("Duende"). Friends become enemies when they fall in love with the same woman and Consone defeats MacLeod in a duel. He spares Mac's life when the girl agress to never speak to Duncan again. Two years later, Duncan returns to Madrid, to find the girl dead and Consone gone. He leaves Europe for America and, by 1854, has returned to the boom town of San Francisco, where he meets a very different Brian Cullen.

The American Civil War finds MacLeod fighting for the Union. He encounter both a child Immortal, ("The Lamb") and a new friend, Lucas Desiree, who rescues him from a grave after he is hung, ("Innocent Man"). His luck does not hold, and he finishes the war a prisoner in Andersonville Prison in Georgia, run by Colonel William Everett Culbraith, ("The Messenger"). He moves to Maryland after the war, but after his lover is killed by her jealous boyfriend, ("Epitaph For Tommy"), he travels to Mexico in 1867 to fight with Paul Karras, ("The Revolutionary"). He returns to the United States and helps a posse hunt down Melvin Koren in South Texas, ("Comes A Horseman"), but Koren escapes from his grave before MacLeod can take his head. Unclear anymore as to why he is fighting and seemingly unable to escape the wars that drove him from Europe and Darius fifty years before, the last straw comes for him the next year in Dakota, when he sees an Indian boy being abused and then killed, ("The Innocent").

He turns his back on the white man's ways and goes to live with the Lacota Sioux, taking care of the wife and son of a friend who dies, ("Line Of Fire") and learning the ways of the wild from Carl The Hermit, ("Mountain Men"). He intends to marry Little Deer, but the gypsies' belief that he will never marry comes back to haunt him when the tribe is massacred by the US Cavalry in 1872, guided by a scout called Kern. Whilst Connor helps him grieve, ("The Gathering"), he is determined to take Kern's head and sets out to hunt him down, becoming as murderous as Kern in the process. He is saved when he encounters the Hayoka, Kol T'ek, who takes his pain from him, ("Something Wicked"). He travels to the Pacific North West for the first time and builds himself a retreat from the Game on holy ground, despite Connor's disapproval. After a visit to Kiem Sun in China, ("Road Not Taken"), he establishes himself as a newspaper proprietor in the Pacific North West, where he again meets Mako, ("Under Color Of Authority"). In 1882, he is killed by the husband of a woman he has fallen in love with and has to leave, ("Obsession"). He works with Gregor Powers during a cholera outbreak, until Gregor is shot by a grieving father, ("Studies In Light").

He moves back to San Francisco, where he spends time with Alec Hill, until Hill's wife is killed, ("Haunted"). In 1888, he stays with Kit O'Brady and, subsequently, Amanda, ("Double Eagle"), still trying to bring Alec Hill back out of his grief. A short career as a prize fighter, at the behest of Tommy Sullivan, ("The Fighter"), is unsucessful and he leaves, arriving in Boston by 1896, where he encounters Axel Whittaker, apparently not for the first time, and young Immortal Sharon Collins, who Axel is using as bait, ("Rite Of Passage"). By 1905, he is established in New York, ("Revenge Of The Sword"), but he returns to Europe when war breaks out.