by Josh Smith
The Pineapple Cup has been through multiple iterations here at the National Tennis Club, beginning with the famed tournament organised by Kip Curren. In its most recent form the Pineapple Cup is the relaxed and low-key cousin of the Pell Cup, giving players an opportunity to enjoy competitive tennis in Newport at both ends of the summer. The field was predominantly NTC, though we were grateful to welcome players from Boston, Tuxedo, Philadelphia, and from further afield, Queen’s Club and Sydney.
Friday and Saturday hosted the group stages; pairs were in groups of four, drawn into their positions in a top half and bottom half based on handicaps. Matches were handicap doubles, first to eight games, with the top two from each group moving on to the knockout stages on Sunday. Wins set the order, with games ratio, before head-to-head, deciding any ties. Those tie breakers would not be required; each group had clear winners who moved through unbeaten, with all second place spots taken by those with two match wins (A: Connor & Harrison Richmond (BOS), Dan Paquette & Chris Werner (NTC), B: Oliver Buckley & Nick Saint (QC, NTC), Jeremy Booth & Chris Doucas (NTC, SYD), C: John Farrell & Chris O’Brien (NTC), Alex Dean & Julia Knowlton (PHI, NTC), CJ Brophy & Doug Rowles (BOS, TUX), Alex Winthrop & Beth Winthrop (NTC)). The group stages were energetic and well fought matches with many of the visiting players moving through to Sunday knockouts, with the NTC Upper East Porch hosting a cocktail party on the Friday, and tournament dinner on the Saturday evening.
The knockout stages had a slower Sunday morning start, partly influenced by the effects of some late Saturday nights, making for some of our most one-sided matches in the quarter finals. The pick of the quarters matches saw Dan Paquette and Chris Werner face off against Oliver Buckley and Nick Saint; the match swinging back and forth over the 14 games played. Paquette and Werner were 7/6 ahead and raced to a 30 – owe 15 headstart with a couple of excellent volley winners, before the score was evened up at 30-30 with equally quick volley errors… Chris Werner hit the shot of the match; a crisp backhand volley under the grille to bring up match point, followed by a mishit serve into the nick to take victory – that’s court tennis! Paquette and Werner were the only second place finishers to progress, the other pairs moving on were our group winners; the Richmond brothers, Farrell/O’Brien, and Brophy/Rowles, all of whom won through in comfortable fashion.
The semi finals were a battle of the handicap heavy hitters. The Richmond brothers faced Paquette and Werner; a rematch from the group stage where the pairs were split by only a single stroke, the Richmond brothers winning the critical 7-all 40-all point. As the match got underway, all players were improving their tennis throughout the morning. Chris Werner and Connor Richmond both drew applause from the dedans after taking turns to mis-read a cut volley, but playing shots behind the back to win the point. The Richmond brothers had the first wave of momentum to give a 4/1 lead, but Paquette and Werner struck back to go 5/4 up. The final swing would prove to be the most significant, with a run of 4 games going to the Boston brothers as they took the match 8/5.
In the second semi final, visitors CJ Brophy and Doug Rowles faced the all NTC pairing of John Farrell and Chris O’Brien, with all the competitors in fine form. CJ and Doug are both relatively new to the sport and put together some of their best tennis in the event, playing to a level that was great value for their respective handicaps. The match was tense and hard fought throughout, as handicap battles often are, with cortisol levels hitting their peaks. John and Chris would not be beaten and with excellent railroad serving from Chris, and volleys at the net from John, they overcame multiple 40 – owe 15 deficits, winning the 7-all 40-all point to take the match and move into the final.
So there we had it. In front of a busy crowd upstairs and downstairs, the final pitted the Richmond brothers, whose dynamic and joyful brand of tennis had entertained and impressed throughout the weekend, against Farrell & O’Brien, the sharply dressed and hard-working pair that had been practicing at 7am for weeks leading up to the event. The match started with a laugh, and indicated the level of attention given to tournament rules as all four players, and the majority of the dedans, showed their surprise at the announcement that the final was a set to 10 games. Farrell and O’Brien had the better start, making the most of some errors from the brothers Richmond that we hadn’t seen over the last five matches. The restes were spirited and high-energy, the court coverage was impressive and committed, with Harrison Richmond ending up on the floor more than a handful of times. The NTC based team would find themselves with a 6/2 lead after an epic rally; John Farrell getting up to the door on the service wall to defend a first gallery chase. At 3/6, the Richmond brothers decided to change receivers. They immediately lost the next game. However, the strategic decision did prove effective; Connor started to drive the ball at John Farrell on the return, forcing some errors from the high net position, and the brothers started to create some momentum. With another enthralling rally finishing with Harrison on the floor once more, the match was tied at 7-all. Predictably tight, the 7 all game was won following a key decision; the Richmond brothers were defending worse than four; a ball floated to length from the receiver’s end was left to bounce and both heads were thrown back in consternation as the ball landed better than four and gave the NTC pair a narrow lead. The next game saw John Farrell defend multiple balls out of the grille and force Connor into some uncharacteristic racquet errors into the net. 9/7. A slight swell of momentum for the home pair. Yet another exciting rally saw Chris shave John’s facial hair with a retrieval, the ball thankfully didn’t make contact, and came to fall tight under the winning gallery and gave match point. Connor forced an error from John to save the first. Farrell serves, overhand and off the side wall, Connor plays cut volley, picking the ball off his toes Chris O’Brien floats the ball down the line, high through the air, finding the grille after wiping its feet on the way in. Game, set, match to Chris O’Brien and John Farrell, who celebrated in front of the home crowd with a roar, leaps and bounds and hands in the air. Congratulations to our Pineapple Cup champions for 2026.
We thank all of our competitors for the valiant efforts throughout the weekend, all matches were played in good spirit and a perfect blend of camaraderie and competition. Commiserations to our losing finalists the Richmond brothers; who left a fantastic impression on the tournament, played excellently throughout. A word to our winners who were incredibly hard working in the lead up to the tournament. As their home pro, it is great to see the players that committed the most hours in consistent, diligent and disciplined practice, were able to reap the rewards in the tournament. We toast to their victory, and to ‘drills!’.
A tremendous thank you to all those NTC members that supported the players, and a sincere thank you to Amy Wintersteen, Kathy Minevitz, and Sewall Hodges, all of whom gave their care, time and effort to help make the tournament enjoyable for all. We look forward to the rest of the summer in Newport, with the Pell Cup up next in mid-August.
