Former Rangers striker Zak Rudden was involved in yet another Scottish Cup upset as Dunfermline Athletic stunned Premiership side Hibernian with a dramatic 1–0 victory at East End Park.
Neil Lennon’s Championship outfit secured their place in the fifth round thanks to a stoppage-time own goal from Miguel Chaiwa, a player currently reportedly attracting interest from Old Firm rivals Celtic.
The late twist sent the Pars through and continued a remarkable run of cup shocks for Rudden, who has now been part of two major upsets in successive seasons.
Although Rudden never made a competitive first-team appearance for Rangers, his name remains familiar to Ibrox supporters. The striker came through the club’s academy and memorably scored in Steven Gerrard’s first match in charge – a 6–0 pre-season friendly win over Bury at Ibrox in front of more than 40,000 fans.
At the time, Rudden was viewed as a promising young forward with the potential to break into the senior squad.
A successful loan spell at Falkirk followed, where his goals boosted his reputation, before a permanent move to Partick Thistle in January 2020 brought his Rangers chapter to an end.
Since then, Rudden’s career has taken him across the Scottish leagues, with spells at Dundee, St Johnstone, Raith Rovers, Queen’s Park and Livingston.
Last season, he was part of the Queen’s Park side that famously knocked Rangers out of the Scottish Cup with a 1–0 win at Ibrox – a defeat that all but sealed the fate of then-manager Philippe Clement.
Now, just a year later, Rudden has again found himself on the right side of a major cup shock, this time helping Dunfermline eliminate Hibernian.
The fourth-round tie followed a classic cup script. Hibs dominated possession but struggled to break down a disciplined and organised Pars side.
Rudden led the line with energy, pressing defenders, holding up play, and helping create space for teammates even as clear-cut chances proved scarce before being replaced by Pars new signing Calumn Morrison after the hour mark.
As the match edged towards extra time, it appeared the Premiership side might eventually find a breakthrough. Instead, the decisive moment went the other way. In the dying seconds, Chaiwa inadvertently turned the ball into his own net following a corner, sparking jubilant scenes around East End Park and sending Lennon’s men through to the next round.
The result carried extra significance for Lennon, who was facing a club he knows well.
The former Celtic boss managed Hibernian between 2016 and 2019, before later returning to Celtic for a second stint in charge.
Dunfermline are now one of the first two teams confirmed in the hat for the fifth round, alongside Rangers, now managed by Danny Rohl, who defeated Annan Athletic 5-0 at Ibrox last night.
The prospect of a meeting between Rudden’s current club and his former employers adds an extra layer of intrigue, given the striker’s recent history in cup upsets involving the Ibrox side.
Elsewhere in the fourth round, Celtic face sixth-tier Auchinleck Talbot tomorrow, while Queen’s Park travel later today to League 2 side Stranraer.
Both will be aiming to join Dunfermline and Rangers as qualifiers for the next stage of the competition.
For Rudden, the night was another reminder that his career path – though it may not have followed the trajectory once expected during his time at Rangers – has been filled with memorable moments.
From scoring in Gerrard’s first match, to helping Queen’s Park eliminate Rangers, and now playing a part in Dunfermline’s latest shock, the former Ibrox striker continues to leave his mark on Scottish football’s most unpredictable competition.