In 1896 he moved to Minnesota in the U.S. where he won the State Championship in 1889. He moved to Spokane, Washington in 1903 where he died on 27 September 1965 at the age of 95.In 1900 he defeated Pillsbury in blindfold simultaneous exhibition given by Pillsbury in Minneapolis, Minnesota. He also won the 2nd Western Chess Association (later the U.S. Open) in 1901. In 2000 he was inducted into the Canadian Chess Hall of Fame.
MacLeod once defeated Emanuel Lasker in a simultaneous exhibition in Quebec. Lasker won 15 games, drew 2 games, and lost one game (to Macleod). The game was something of an oddity because Lasker refused to resign even though he was down by two queens.
Macleod's career wasn't all studded with success though. In the 6th American Chess Congress held in New York in 1889 he won 6 games (including one against Joseph Blackburne) and drew one but lost a whopping 31 games, finishing in last place. 38 games in one tournament?! It was a 20-player double round robin making it one of the longest tournaments in history.
In the first half of the tournament, draws were counted as a half point. In the second half, they were replayed once. Between the 38 regular rounds, 8 replay rounds, and 4 game playoff for first at the end, there were 50 rounds in all!
Actually the tournament consisted mostly of foreign masters and the top American finisher was Solomon Lipschutz, who finished in 6th place with a score of +22-9=7. The top places were taken by Weiss, Chigorin, Gunsberg, Blackburne and Burn.
Chessmetrics gives his highest rating as 2396 on the May 1892 rating list which put him at number 82 in the world. Surprisingly his best performance was 2350 at the New York, 1889 event despite losing 31 games. That's because his opposition averaged 2595.
In addition to his world record setting number of losses at the 6th American Congress, MacLeod also seems to hold another dubious distinction...after looking at a few of his games, mostly losses, I was able to find one that was particularly interesting, so for the record I am posting his defeat of Lasker with minimal notes.