Sport & Entertainment
JAM | May 17, 2025

From Portland to Germany: Chester Senior’s dream UCL trip with Heineken

/ Our Today

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Chester Senior

For any lifelong football fan, the dream isn’t just to watch a match on the big screen—it’s to feel the roar of a stadium live and in action. Thanks to Heineken’s UCL Hardcore Fan Experience, that dream came true for 52-year-old Portlander Chester Senior.

Chester, a self-proclaimed football fanatic, has been in love with the game since his father showed him a tape from the 1968 World Cup match, dreaming of one day becoming a footballer himself. “While most boys amused themselves with marbles or games of hide-and-seek, I was outside, tirelessly chasing anything remotely round that could pass for a ball,” said Chester. 

As the years passed and fatherhood arrived, Chester found himself sharing his passion for the sport with his eldest son, despite their divided loyalties—Chester’s heart beats for Liverpool, while his son roots for Chelsea. However, the shared experience remains a treasured bond.

“For any father, that’s a tough pill to swallow,” he laughs. “Your dream is to bond with your son as your team competes – and instead, he’s on the other side of the pitch!” Their rivalry fuels a playful banter, with Chester quick to remind him, “Liverpool has beaten Chelsea eighty-six times.”

But even amid the friendly competition, Chester is always game for moments that bring them closer—especially when football is involved. So, when the Heineken UCL contest launched earlier this year, Chester felt certain—this was his moment. “If there’s no Heineken in my fridge, then clearly, something’s not right,” he remarked with a playful grin. While picking up a case at his local supermarket, the cashier mentioned the contest. He entered on the spot – and the rest, as they say, is history.

When the call came through announcing that he had won the grand prize—an all-expenses-paid trip to Germany—Chester was stunned into disbelief. A lifelong football enthusiast who routinely sacrifices sleep to catch late-night matches and can recite Liverpool and Arsenal statistics with greater ease than birthdays, he is the embodiment of true sporting devotion.

“Football is everything to me. I don’t miss matches. I enjoy the sport every time a game is on TV. To finally sit in a stadium, in another country, and watch the action up close? That’s the stuff of dreams. I’m beyond grateful to experience this.”

Over the years, that passion of his has extended to his wife. Though she will not be joining him in Germany later this month, he’s already made birthday plans to take her on a European adventure of her own. For now, this trip is a gift to his inner child, a dream fulfilled.

As he prepares to get off later this month, Chester looks forward to cheering on Paris Saint-Germain F.C. (PSG). “I’m backing them to win the Champions League,” he chuckled, acknowledging also his tendency to switch allegiances, a trait not uncommon among football fans when their teams endure too many defeats.

“I’ve been to stadiums before, but nothing like this,” Chester continued, his voice tinged with excitement. “I’ll be in a venue twice the size of ours, surrounded by passionate fans who love the game as much as I do. I’m going to meet new people, share stories, and fully immerse myself in the experience.”

For Chester, this trip is a tribute to a lifetime of unwavering devotion to the game. The lights, the chants, the energy, the unity—he knows these will further ignite the very spark that first captured his heart all those years ago. “This isn’t just about a free vacation for me,” he said, his voice growing more earnest. “It’s a celebration of everything that makes me love this game. It’s fuel for my passion.”

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