![Federer to play Hewitt in world first for Sydney | 25 November, 2014 | All News | News and Features | News and Events | Tennis Australia Federer to play Hewitt in world first for Sydney | 25 November, 2014 | All News | News and Features | News and Events | Tennis Australia](https://www.tennis.com.au/wp-content/uploads/2014/11/Fed-Hewitt-cropped-700x450.jpg)
Federer to play Hewitt in world first for Sydney | 25 November, 2014 | All News | News and Features | News and Events | Tennis Australia
![Roger Federer was awfully tough to play in big matches" - Lleyton Hewitt on his most difficult opponents Roger Federer was awfully tough to play in big matches" - Lleyton Hewitt on his most difficult opponents](https://staticg.sportskeeda.com/editor/2020/10/49772-16017155271362-800.jpg)
Roger Federer was awfully tough to play in big matches" - Lleyton Hewitt on his most difficult opponents
![Going head-to-head with two all-time greats in Roger Federer and Rafael Nadal in their prime made it challenging" - Darren Cahill on Lleyton Hewitt Going head-to-head with two all-time greats in Roger Federer and Rafael Nadal in their prime made it challenging" - Darren Cahill on Lleyton Hewitt](https://staticg.sportskeeda.com/editor/2022/07/208d2-16580430040464-1920.jpg?w=840)
Going head-to-head with two all-time greats in Roger Federer and Rafael Nadal in their prime made it challenging" - Darren Cahill on Lleyton Hewitt
![Through 2003, Hewitt lead his head-to-head with Federer 8-2. When Hewitt retired, he was trailing the matchup 9-18. : r/tennis Through 2003, Hewitt lead his head-to-head with Federer 8-2. When Hewitt retired, he was trailing the matchup 9-18. : r/tennis](https://external-preview.redd.it/ckvSjJGkaez3vXYaxNCFpcsIeNEfEVK3cK8eFqmWESY.png?auto=webp&s=a2f2a7cb781229e8e3399084c19439b4d3d13fe9)