David Humphreys' boot found the target in the most dramatic fashion imaginable—a drop kick that rattled off both posts before tumbling over the bar to hand Ulster the Celtic League in 2006, and now, 20 years later, the province is chasing that feeling again.

When Ulster lifted their last trophy nearly two decades ago, Tommy Bowe was certain it was just the beginning. "We thought that this is what you do with Ulster Rugby, that you come in and play some great rugby and go on to win lots of trophies," he recalls. But the intervening years have been marked by heartbreaking near-misses and an aching silence—no silverware since that unforgettable day in Swansea. The province has come agonizingly close to breaking that spell, yet somehow always fallen short. Now, on Friday night in Bilbao, they face Montpellier in the Challenge Cup final, a last chance to transform what would otherwise be a season of progress into one of genuine achievement.

The 2006 triumph remains etched in Ulster rugby folklore with good reason. That Celtic League victory came after Ulster's earlier European Cup fairytale in 1999, but it was the domestic breakthrough that truly mattered to the province. The manner of Humphreys' match-winning kick has only grown more legendary with time. When the team gathered for a 20th anniversary celebration last week, with more than 30 players and staff from that squad in attendance, the stories flowed freely. Andrew Trimble admitted he'd grown up with a poster of Humphreys on his bedroom wall, yet only when rewatching the highlights at the reunion did he realize his childhood hero had "a stinker" of a match before that decisive moment. "The day was kind of about him and those three points," Trimble laughed, the humor masking the weight of what that single kick meant.

That 2006 squad was a masterclass in blending experience with emerging talent. Veterans like Humphreys, Justin Harrison, and Justin Fitzpatrick anchored a group that included bright young players—Bowe, Andrew Trimble, Rory Best, and Stephen Ferris—who would go on to become legends in their own right for Ulster and Ireland alike. The chemistry was unmistakable. Harrison, now performance director of the Irish Rugby Football Union, speaks of how essential it was to buy into Ulster's proud identity from the moment he arrived. "It's very important when you pull on a jersey to represent Ulster, it's serious," he said at the reunion. The commitment ran so deep that scrum-half Isaac Boss flew in from New Zealand for just 24 hours to celebrate with his former teammates.

Now Ulster must break their two-decade drought against a formidable opponent. Montpellier, a two-time Challenge Cup champion and currently second in France's hotly contested Top 14, will come to San Mames Stadium as heavy favorites. Ulster, by contrast, dropped out of the top eight of the United Rugby Championship on the final day of the season. Yet manager Richie Murphy's team arrives with momentum from an impressive semi-final win over Exeter Chiefs, and Bowe believes they possess the tools to upset the odds. "This team is more than capable of playing a really exciting brand of rugby and running this Montpellier team around," he said. A victory would secure not only Ulster's first trophy in 20 years but also Champions Cup qualification—silverware and a return to Europe's top table in one stroke. A loss means heading home empty-handed, the long wait extending further still.