Like so many Canadians, I cheered along as Milos Raonic fought back for famous victories against David Goffin of Belgium, and Roger Federer of Switzerland. This was a wonderful thing for Canada…a Canadian in the Men’s Final at Wimbledon. Surely this was something for all of us to get behind, cheering him on.

Except for this: his opponent in the Final was Andy Murray of Scotland.

I was born into a keen tennis-playing family in Scotland. I was good enough that I was on the local Men’s Team at 14, and my father and I never lost a set all season, as our fit young opponents vacillated between picking on the old guy, or targeting the little kid. So after I came to Canada in 1967, as my own minor tennis career  came to an end, I watched Andy Murray’s career take off, and supported him keenly – although watching him was never a truly relaxing experience.

He played a part in my own career as a writer. In 2008 he made it to the Final of the U.S. Open in Forest Hills, his first Grand Slam Final. I happened to be in Scotland, staying with my brother’s family near Stirling, just south of Dunblane, Andy Murray’s home town. Shazam! It was time for a piece of enterprise reporting. I contacted the Globe and Mail and asked if they would like a Special Correspondent’s Report on watching the New York Final in Andy Murray’s home town.

They liked the idea. I grabbed a quick sandwich, while my young nephew watched in disbelief (“You’re just going to go there and write about it for the newspaper?”), and drove to Dunblane. Quick questions on the street revealed that the tennis match would be shown at The Dunblane Community Centre. I found it, found the organizer, and shamelessly introduced myself with the words “I represent the Globe and Mail newspaper in Toronto”. In turn, she introduced me around in the crowd, to friends of the Murray family. I knew that all would be well when one old gentleman gave me the quote “Win or lose, to me Andy will always be just a wee laddie from Dunblane.” (Punching the air is not an appropriate response from a note-taking reporter).

Well, Andy didn’t win that day, but The Globe and Mail’s readers got a fine feature from an unexpected tennis correspondent. If you don’t believe it, you could look it up, from September 2008.

So Andy Murray and I go back a long way. Supporting Milos against him was going to be very hard. It was indeed, as my title suggests, a real tennis conundrum. How should a patriotic Canadian born in Scotland handle this culture clash?

In the end, I decided that since both Scottish and Canadian cultures are, let’s say “anti-triumphalist”, my most appropriate position was to support, and root for, the player who lost in the end.

So go, Milos!