Jockey Derek O’Connor bridged a 23-year gap by landing Monday evening’s featured Connacht Hotel Handicap on board the Joseph O’Brien-trained Comfort Zone.The most successful ever point-to-point rider was claiming a 7lb allowance in 2003 when landing Irish racing’s ‘amateur Derby’ on Rapid Deployment. Over 1,400 point-to-point winners later, multiple Cheltenham Festival winners, and widespread recognition as one of the country’s best ever amateur jockeys, O’Connor once again secured the prized €110,000 highlight.At 44, O’Connor has 11 years on the winning trainer. But on a gloomy opening to the summer festival, Comfort Zone’s 18-1 victory was a shiny new landmark for O’Brien, who completed his set of Galway’s feature contests.Twice successful in the Galway Hurdle, O’Brien won the 2020 Plate with Early Doors and the big Mile with Mexicali Rose two years ago. Even the Corrib Stakes and the Ahoonora Handicap have fallen to him in the decade he’s been training.O’Connor and O’Brien memorably teamed up in 2018 for an Irish Gold Cup success with Edwulf, and even in the context of the trainer’s Oaks successes with Thundering On and Johanna Walsh, this was a summer big-race success to savour.“To win the feature on the Monday night is very special and it sets up the week,” O’Brien said. “Derek is a fantastic rider and it was great to have him on board. It looked a bit messy during the race and into the dip it looked a rough enough race. [But] Derek got a wide run around them.”Colin Keane on Madbadanddangerous wins The Grá Chocolates Handicap at Galway. Photograph: Morgan Treacy/Inpho That sort of big-race savvy has always been in O’Connor’s locker, and the reigning point-to-point champion, based just 20 minutes from Ballybrit, held on by three parts of a length from the 40-1 topweight Holy See, with the 2023 winner Teed Up in third.“It’s so competitive with such a high calibre of amateur rider riding in Ireland at the moment and such a high calibre of horse competing in the race,” he said. “To get nice rides off Mr [JP] McManus and Joseph O’Brien, you are not tied to instructions, so you have a free hand.”O’Brien wasted no time doubling up in the following flat handicap as Dancing Saxon made light of topweight. Dylan Browne McMonagle brought the filly from the rear to score by over four lengths. Fresh from his King George success on Kalpana, Colin Keane produced another topweight, Madbadanddangerous, to pounce late in a 12-furlong handicap for Noel Meade.Paddy Twomey has big-race ambitions for his impressive juvenile maiden winner Trean, who was almost five lengths too good for City Of Gold.“He’s in the National Stakes, he’s in pretty much everything,” the trainer said.Witches Familiar won a second hurdle race in the summer festival opener and showed enough quality to suggest she could have a winter campaign in front of her.“We’ll up her in grade as best we can. I’d probably be looking at her as a Royal Bond-type filly,” Willie Mullins said. “I can see her being a good mare in novice company for the whole season. I’d be looking at the long term rather than shorter term with her.”Otherwise, it was a grim opening to the week, with both Carmel’s Phoenix and Munsif, joint-second favourites, sustaining fatal falls.The opening day attendance of 16,102 was down from last year’s corresponding figure of 18,472.Séamie Heffernan on Dunum (left) winning last year's Colm Quinn BMW Mile at Galway. Photograph: Morgan Treacy/Inpho It’s a typically competitive renewal of Tuesday evening’s featured Colm Quinn BMW Mile, where last year’s winner Dunum is back for another crack at the €120,000 contest.Natalia Lupini’s stalwart is 3lbs higher in the ratings this time and has a double-digit draw. A low draw is generally a positive around this tight circuit and Dunum exploited stall two last season. The 2024 winner Mexicali Rose broke from box one.It’s not a theory set in stone, however, as the previous seven winners all came from a double-digit position. That’s good news for the sole Mullins runner, Kai Lung, who is in stall 19 on his first flat start for the champion jumps trainer.Mullins’s Riven Light came from 18 on the second of his wins in the race in 2018, while Magic Chegaga won from 19 in 2022. Declan McDonogh is getting down light for the spin on the bottom-weight that has winning form in France.Aidan O’Brien runs two in a juvenile maiden won in the past by subsequent Classic winners Tahiyra (2022), Hermosa (2018) and Legatissimo (2014). Paddy Twomey scored with Purple Lily three years ago and unveils a €380,000 purchase, The Good Wife, who holds some fancy entries.O’Brien’s Group One focus on Tuesday is on Scandinavia, who bids to win the Goodwood Cup for a second time. Ryan Moore’s mount renews rivalry with Trawlerman, who he beat in an epic Ascot Gold Cup duel last month.