Chris Callis and Sam Khalifa, the second seeds, claimed the title with a 3–1 victory over top seeds Scott Arnold and James Stout, winning 11–15, 15–6, 15–6, 15–8. After many years of hosting the Bentley Cup as a high-profile invitational, this was the moment to sanction it as an SDA World Ranking event, ensuring the strongest teams currently competing would take part. Now that the dust has settled and the club has witnessed the highest level of doubles squash in the world, it is clear that this was the right decision. The range of styles, the raw power, the athleticism, the outrageous retrieving, and the shot-making that drew audible gasps from the gallery all came together to create a weekend of exceptional squash.
Saturday at the 52nd Hampton Securities Jim Bentley Cup delivered a full slate of matches and yet another ultra-competitive shootout that came down to the final point. Before play began, Caesars were circulating courtesy of the Oak Room staff, a medicinal tonic to soothe the lingering effects of yet another highly successful Black Tie extravaganza. Fortunately, the pros had kept their discipline and retired early enough to be prepared for the day’s battles.
The quarter-finals opened with local favorite Scott Arnold and his partner James Stout, the top seeds, facing the youthful firepower of Jackson and Josh Kay. The Kay brothers came out flying, catching the favorites off guard and racing to a 15–5 opening win. Arnold and Stout responded with patience and length, found their rhythm, and closed out the next three games to book their place in the semis. Immediately afterward, Josh Kay jumped in the car and sped off to play for Western against powerhouse Harvard at Ridley College as part of the celebrations around their new facility.
Next on court was the legendary John Russell, one of the veterans of the tour whose squash IQ remains elite. Russell, one of the best doubles players of the last decade, reads the game like Gretzky, carries Federer’s hands, and still moves with authority when needed. His partner, Colin West, had tweaked his calf earlier in the week but managed to bandage himself into a state of being only slightly faster than everyone else. They took on the eighth-seeded pairing of Mike Ferreira, owner of a deceptive two-handed backhand, and Cam Pilley, the world’s hardest hitter of a squash ball. The match was tight throughout, but the mobility issues of the Russell-West duo told in the big moments, and Ferreira and Pilley battled through to score the upset and reach the semi-finals.
In the third quarter-final, the tenth seeds Daelum Mawji and Charles Culhane faced third seeds Kyle Martino and Josh Hughes in what resembled an Ivy League scrimmage. Both teams chose power over subtlety and hit every ball as hard as possible, with bursts of creativity from the unorthodox left-hander Hughes. Culhane and Martino fought a territorial war on the right wall while the Caesar-fueled crowd pounded the glass. Once again, the match came down to the final point, and Martino and Hughes edged through to advance.
The final quarter-final featured defending champions and lifelong Cambridge Club members Robin Clarke and Matt Henderson against second seeds Chris Callis and Sam Khalifa. Khalifa’s all-court skill and Callis’s command of the right wall T were on full display, but Clarke and Henderson pushed hard, stealing the second game and drawing huge support from the home crowd. Ultimately, Khalifa’s relentless length and control wore down Clarke, and Callis and Khalifa moved through to the semis.
By the time the semi-finals arrived, both Ferreira-Pilley and Martino-Hughes were showing the effects of their earlier dogfights. Both top-seeded teams settled into routine wins, each advancing in straight games to set up the final everyone expected: the legendary duo of Arnold and Stout against the explosive creativity of Khalifa and the positional mastery of Callis. World No.1 versus World No.2, club royalty versus a surging partnership — the perfect script for the 52nd Hampton Securities Jim Bentley Cup.
Arnold, beloved at the club for his understated professionalism and immaculate preparation, has long been one of the very best players in the world, balancing his duties as GM and Head Pro at the TRC with his dominance on the doubles court. Stout, a master of Racquets and one of the finest Real Tennis players globally, has also committed himself to doubles, forming with Arnold the team to beat for several years. Their opponents, Khalifa and Callis, brought their own imposing credentials: Khalifa, in only his third year on the tour, already one of the best doubles players; Callis, a Princeton star and former dominant force alongside Manek Mathur, now revitalized in his new partnership after health challenges.
The final began with both teams probing for weaknesses. Callis made a few early errors, and Arnold and Stout capitalized, taking the first game 15–11. In the second, Callis and Khalifa shifted gears, relying on patience and length. Callis held the middle of the court like a brick wall while Khalifa pounced on anything loose, carving in breathtaking drops. They controlled the entire game and leveled the match with a 15–6 win. In the third, Stout tried to push Callis off the T with high, lifting play, but Khalifa produced some of the most extraordinary retrieving and shot-making the crowd had ever seen. Several rallies could have swung either way, but the biggest points went to Callis and Khalifa, who took the third 15–6 despite the razor-thin margins. With momentum fully on their side, the Ivy Leaguers continued their surge, and while Arnold and Stout landed some brilliant blows, Callis and Khalifa remained in full flow, taking the fourth 15–8 and securing the title.
What ultimately separated the teams was the run of five or six massive rallies in the third game that swung the momentum irreversibly. The quality was extraordinary, and the crowd appreciated every moment — none more so than the newly crowned Squash Member of the Year, whose uncanny run of Calcutta success continues to raise eyebrows and delight the Polo syndicate.
As always, the Bentley Cup is far more than a tournament; it is a club achievement that reflects the dedication of members, staff, volunteers, sponsors, and the entire Cambridge community. From Mike Deeb’s nearly two-decade commitment as Title Sponsor through Hampton Securities to the many new and returning members who stepped up to support the week, the Black Tie Extravaganza and the championship itself showcased the spirit, generosity, and joy that define the club.
A heartfelt thank-you goes to everyone — members and staff, players and supporters — who contributed to another unforgettable edition of the Jim Bentley Cup. This event is for all of you.