“It was great to wake up with a dream every day — mine was to play at the Grand Slams,” said Conor Niland. Though he got to like that dream for a little while, it soon turned into a bittersweet memory. Niland never became a household name like Roger Federer or Novak Djokovic. But he was once in their orbit, brushing past the game’s giants in ways most players only dream of. Then he ultimately left to pursue a career in real estate. But an almost meeting with the Swiss Maestro still haunts the Irishman.

He started with a bang. As a 12-year-old from Ireland, a country with barely any tennis tradition, Niland managed to beat Federer in a friendly at the Winter Cup youth tournament in 1994. It wasn’t a headline-grabbing match, but for Niland, it was a sign he could hang with the best. That dream carried him through years of hard graft on the professional circuit. He clawed his way to the Grand Slams, but his outings ended early. At Wimbledon in 2011, he had a 4-1 lead in the final set against Adrian Mannarino. A win would have set up a Centre Court match against Federer, but the dream was lost.

He has penned it down in his book ‘The Racket’, and it still stings. “I sometimes felt like tennis hated me. I think about the Mannarino match that I lost at Wimbledon every day, more or less,” Niland said in an interview according to Express.co.uk.“To have played Federer at Wimbledon would really get people’s attention but the fact I lost that match has made the book a lot more interesting and changed the whole narrative of the story.” 

The heartbreak didn’t end there. A few months later at the US Open, Niland was trailing Novak Djokovic 6-0, 5-1 on Arthur Ashe Stadium when food poisoning forced him to retire. That was as close as he ever got to the titans of the sport. The following season, aged 30, Niland stepped away from tennis. A persistent hip injury had worn him down. He left with a career-high ranking of World No. 129.

But his tennis story wasn’t quite over. Niland turned to writing, and in 2024, he released his autobiography, ‘The Racket’. The book was a raw and honest look at what life is really like for tennis players who live outside the spotlight. It wasn’t all locker rooms and press conferences, but it was long-haul flights, lonely hotels, and scraping for points and prize money.

Conor Niland’s book unpacks life outside of top players like Roger Federer

In ‘The Racket’, Niland didn’t just revisit the near-misses. He also pulled back the curtain on tennis’s harsh financial reality. He talked about the vast money gap between the top players and those grinding it out on the lower rungs. “It’s not good enough that there aren’t 300, 400 people in the world, men and women, who can make a very decent income,” he said, pointing to golf as a better-paying comparison. Niland knows the numbers better than most. During his seven-year pro career, he won three ATP Challenger titles and five ITF Futures tournaments. Yet he admits he spent those years “bouncing from one country to the next” just to keep going.

Pay discrepancy has been a major talking point in tennis recently. French publication L’ÉQUIPE reported that the top 20 male and female players collectively signed and sent a letter to the GS organizers, demanding a major prize money overhaul.

‘The Racket’ won the William Hill Sports Book of the Year Award, for which the 43-year-old won £30,000 ($40,236). That figure is double Niland’s biggest single payday during his time as a pro. The win was not only a recognition of his writing but a full-circle moment. His biggest paycheck didn’t come from the sport he dedicated his life to; it came from telling the story of how tough that life really was.

Now, Niland lives in Dublin with his wife and two kids, Emma and Tom. Both kids play tennis, though he himself rarely picks up a racket anymore. He’s connected to tennis, though, as he coaches the Irish Davis Cup team. But his main focus remains on commercial real estate. He’s an Associate Director of Retail and Leisure at Cushman & Wakefield, one of the world’s biggest real estate services firms.

Conor Niland didn’t get that Centre Court match with Roger Federer, but he found another way to make his mark. Sometimes the best stories are the ones that don’t end with a trophy.