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The Last Winner Of The Grand Challenge Cup?

11th June 2026
Silver Legacy – First awarded in 1948, the Grand Challenge Cup became the premier prize of the Isle of Man Midnight Race for more than 70 years. The trophy remains part of Tranmere Sailing Club's collection. Photo: Tranmere Sailing Club
Silver Legacy – First awarded in 1948, the Grand Challenge Cup became the premier prize of the Isle of Man Midnight Race for more than 70 years. The trophy remains part of Tranmere Sailing Club's collection Credit: Tranmere Sailing Club

Seven years after winning one of the Irish Sea's oldest offshore races, Chris Power Smith may still be waiting to pose with the trophy that came with victory.

The Royal St George Yacht Club skipper's Aurelia won the 100th Isle of Man Midnight Race in 2019, a landmark edition of a race first sailed in 1907. Yet a global pandemic intervened, the prizegiving never happened, and the future of the race's historic Grand Challenge Cup took an unexpected turn.

The Liverpool to Douglas race is among the oldest offshore yacht races in these waters. First held on 24 May 1907 by Liverpool Bay Yacht Club, it predates the Fastnet Race by almost two decades and has survived two world wars, severe weather and changing eras in yacht racing.

The original race attracted 11 yachts from clubs around the Irish Sea. Competitors raced from New Brighton Pier to Douglas for a silver epergne weighing 88 ounces, while every finisher received a commemorative silver medal.

The race's history is filled with colourful stories. In 1935, only one yacht, Kathleen, completed the crossing after competitors encountered severe weather. A year later, sailors relied on weather reports relayed from Isle of Man Steam Packet vessels and transmitted to shore by Morse code before the start.

Tranmere Sailing Club assumed responsibility for organising the race in 1925 and remained its custodian for decades.

The story emerged after ISORA Chairman Peter Ryan contacted Afloat following coverage of this year's Liverpool to Douglas race. Ryan highlighted the significance of the Midnight Race's history and pointed to the Grand Challenge Cup as one of its most notable traditions.

Further enquiries, however, revealed that while the trophy remains an important part of the race's heritage, it is no longer awarded to the winner. According to Liverpool Yacht Club, the Grand Challenge Cup remained with Tranmere Sailing Club after administration of the race transferred to Liverpool Yacht Club in the early 2020s.

In 1948, according to Tranmere Sailing Club's published history, Percy Christian presented what became the race's most famous prize — the Grand Challenge Cup. The trophy was awarded annually to the overall winner and became synonymous with the Midnight Race.

By 2019, the race had reached its centenary running. Conducted in association with the Royal Ocean Racing Club and attracting 43 entries, it was one of the most significant editions in the event's history.

Power Smith's Aurelia emerged victorious.

"We won the 100th anniversary Midnight Race, part of the RORC calendar that year with 43 entries, and that came with the Challenge Trophy," Power Smith recalled.

"Unfortunately we had to cancel our trip to the presentation at the Liverpool Yacht Club annual dinner due to Covid."

The trophy itself carries its own fascinating history. Liverpool Yacht Club Commodore Nichola Murphy, citing information supplied by former Commodore and current Vice-President Paul Hampson, said the Grand Challenge Cup was first awarded in 1948 and was last won by Aurelia in 2019.

According to Liverpool Yacht Club, the trophy is a silver copy of the Warwick Bowl, a Roman marble vessel discovered near Hadrian's Wall and now housed at Warwick Castle.

Power Smith was told that one of the trophy's claims to fame was a connection with the Australian Open men's championship trophy. Liverpool Yacht Club says this link remains unverified, although the resemblance between the cups has long been noted.

The story took another turn in the early 2020s.

According to both Liverpool Yacht Club and Tranmere Sailing Club records, administration of the Midnight Race passed to Liverpool Yacht Club. Murphy said Tranmere Sailing Club retained ownership of the Grand Challenge Cup, while Liverpool Yacht Club continued to organise the race.

New Era – 'Bobby', Liverpool Yacht Club's silver Liver Bird trophy, now serves as the principal prize for the Isle of Man Midnight Race following the transfer of race administration in the early 2020s. Photo: Liverpool Yacht ClubNew Era – 'Bobby', Liverpool Yacht Club's silver Liver Bird trophy, now serves as the principal prize for the Isle of Man Midnight Race following the transfer of race administration in the early 2020s. Photo: Liverpool Yacht Club

A new era brought a new trophy.

Liverpool Yacht Club commissioned a silver Liver Bird trophy crafted by Liverpool silversmiths R&R Porters. Affectionately known as "Bobby", it now serves as the race's principal prize, with pewter replicas awarded across several categories.

The Grand Challenge Cup, meanwhile, remains part of Tranmere Sailing Club's trophy collection.

Final Holders? – Chris Power Smith's J/122 Aurelia won the 100th Isle of Man Midnight Race in 2019. According to Liverpool Yacht Club, it was the last race for which the Grand Challenge Cup was awarded. Photo: Afloat.ieFinal Holders? – Chris Power Smith (pictured kneeling) and his J/122 Aurelia crew won the 100th Isle of Man Midnight Race in 2019. According to Liverpool Yacht Club, it was the last race for which the Grand Challenge Cup was awarded. Photo: Afloat.ie

Although Aurelia won the Grand Challenge Cup in 2019, Power Smith never had the opportunity to collect it after Covid disrupted the planned presentation.

"I was told I would be the last person to win it," he said.

Whether Chris Power Smith will ever get the opportunity to stand beside the Grand Challenge Cup remains unclear. What is certain is that Aurelia's victory in the 100th Isle of Man Midnight Race marked the end of an era.

After more than 70 years as the race's premier prize, the Grand Challenge Cup passed into history, leaving one lingering question for Irish Sea sailors: will its last winner ever get to hold it?

Published in ISORA
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