OTW Extra Email Archive - September 2026
Notes from the Tour: Crystal Ball Polishing Service...
Wednesday 16th September 2026
The year is 2002, and a young player named Roger Federer is playing in the 1st round at Wimbledon…
Roger lost that match. Dumped out in the 1st round by Croatian qualifier, Mario Ancic. A particularly galling result for a great old friend and colleague of mine – the man I regard as my mentor in this betting business, who had backed Federer at big outsider odds…
The gentlemen in question, who is very sadly no longer with us, ran a betting advisory service long before I’d even started. Every now and then, he would write up a special article, which he called ‘The X File’ – telling members about an up-and-coming player who he believed was about to make it big. Roger Federer was one of those. ‘One to Watch’ – you might say…
The very next summer, in 2003, Federer won his first Wimbledon title. And he went on to win SW19 five times in a row on that streak. Collecting a total of eight Wimbledon titles by 2017.
My old friend. The wise wizard. He picked out Federer ‘too early’…
But he also got it bang on many times, too. Ever heard of Novak Djokovic? My man tipped Djokovic at 33/1 when the Serb won his first ever Grand Slam trophy, at the Australian Open in 2008.
The early bird gets the worm. It’s a phrase I live by in this game…
I went ‘too early’ with Linda Noskova. Backing the young Czech for Wimbledon at 150/1 in 2024… then at 66/1 last year… only to see her take the maiden Major crown this summer, instead.
Or how about Ben Shelton, who just last weekend reached his first Grand Slam final, at the US Open? The American started the tournament as one of the favourites, at 10/1. I backed Shelton for the US Open in 2024 at 80/1 (where he lost in the 3rd round)…
Should I also tell you all about a young Spaniard called Carlos Alcaraz? I backed him as an early-bird selection for the Australian Open 2022, at 33/1. He went out in the 3rd round in Melbourne that January… but by the end of the year, he’d won his first Major, having gone off at just 5/1 to win the US Open.
And just like my dearly departed friend and mentor – sometimes I get it very right, on time, too...
Iga Swiatek in 2020… Madison Keys in 2025 (both 100/1 winners)…
Now, looking forward…
If I consult my ‘near miss/ youngsters’ list from this year’s Grand Slam picks. I’d say that you and I should keep a close eye on the likes of Marta Kostyuk, Karolina Muchova, and Iva Jovic at the 2027 ‘Slams. To name just three…
With plenty of big tournaments still to come on the ATP and WTA Tours this autumn. Including the start of the Asian swing in China next week…
Not a member yet? Join Ones to Watch here…
Enjoy the tennis…
Best wishes,
Oliver Upstone