Partnering Helen Rees' 11-year-old gelding Bart VI, Wingrove was positioned towards the end of a 17 horse second round.
Irish contenders Stephen Moore (Cristobar) and Philip McGuane (Judas Vd Donkhoeve) had set the pace early on and held the top two places until Joseph Clayton brought the competition alive, jumping clear with Millioninmind and clocking a time of 42.83 seconds.
Jumping in reverse order of their placings from the first round, the crowd knew that the competition was far from over and next in to the arena, Graham Lovegrove proved this point, moving into the lead with Centolove after knocking over a second off Clayton's time.
Jamie followed with Bart VI and went straight to the top of the leaderboard in a blistering time of 41.20 seconds. Jessica Dimmock and Cassius Clay were unable to match this pace and slotted in to third place in the final standings while an unlucky fence down for first round leader Emily Ward and Doobally dropped them out of contention.
'I watched a couple of the earlier riders go and knew it was going to be a tough competition,' said Wingrove speaking after his win. 'Usually if Bert leaves the fences up he's there or there abouts and today he did! This is my first time at Bolesworth and it's been an unbelievable show – Nina and her team have thought of everything.'
Earlier on Saturday, Wingrove had come out on top in the 1.30m CSI2* Table A class sponsored by Watson Plant Hire which kicked off proceedings in the Castle Arena. Speed was the name of the game and pathfinders for the class, Eve Stavely and Shadow IV set a target time of 73.26 seconds which kept her at the top of the leaderboard until Wingrove entered the arena with Heartstring.
Eleventh to jump, Wingrove bettered the target by nearly six seconds to go into the lead on 67.67 seconds with the seven year old gelding owned by Georgia Reynolds. Jamie and Heartstring came to Bolesworth off a good run of recent form on the Mediterranean Equestrian Tour and closer to home in the CSI*YH classes at Arena UK.
'Heartstring qualified for the Foxhunter Final a few weeks ago so we brought her to Bolesworth for an easier show,' said Wingrove. 'She had a nice canter around and ended up winning!'
Several riders that followed came close to taking the lead including USA rider and Bolesworth first timer Brieanne Dofort who posted a time of 71.68 seconds which was good enough for third place in the final standings. As the class reached its final stages, Surrey-based rider Stuart Neads gave his best effort to overtake the leader but a time of 68.93 seconds saw him settle for second place with the Hill House Equine owned seven year old mare Freya.
The 1.40m Jump-Off class presented in association with The Brooke (Bolesworth Charity of the Year) brought the action in the Castle Arena to a close and out of the fifty six starters, just fourteen made it in to the deciding round.
An early draw proved no disadvantage to Hampshire rider Sienna Charles who partnered father Peter's 10-year-old mare Chaitanya 2 to victory with a jump-off time of 42.37 seconds. With just four combinations recording a clear second round, Charles maintained a four second lead over her opposition at the end of the class with Belgium's Cyril Cools coming closest to overtaking the leader when clocking 46.32 seconds with the Amandine Wittouck owned Vendetta Treize. A time of 46.40 seconds was enough to secure a podium finish for Daniel Neilson who took third place with Stacy Willsone's Cirrus.
'I knew I could go fast enough but the people behind me were very experienced' said Sienna after her lap of honour. ' I just had to move up wherever I could. There were some tricky lines and I took a stride out at the triple bar.'
'I've had Chaitanya 2 for nearly two years, she's called Flicka in the stable. She's really greedy and goes crazy for bananas at home!'
'My horses will have a week off now before we head to Knokke in Belgium for three weeks.'