1. Barbados vs Grenada (1994)
In this qualifier for the 1994 Caribbean Cup, Barbados needed to win by a two-goal margin in order to qualify for the finals.
However, a new rule tested by the cup’s organisers somewhat complicated things. It stated that a period of 'Golden Goal' extra time should be used to decide any match that was tied after 90 minutes.
That might not sound too crazy, until you consider the fact these were 'round robin' matches, rather than a straight knock-out. Also, any Golden Goal would count double – important, given goal difference could help determine the final standings of the group.
Barbados had their required 2-0 scoreline until a few minutes from the end, when Grenada pulled one back in the 87th minute. The hosts had to regain their winning margin, but rather than push for a dramatic decider in the dying seconds, their quick-thinking players realised that it would actually be better to score an own goal and force extra-time, which would give them longer to secure victory by a two-goal margin (which they'd achieve by scoring once – still with us...?)
One of the Barbados players wellied the ball into his own net, but then things only got weirder. Grenada quickly realised that a goal at either end in the remaining minutes would win them the group, and thus Barbados were forced to spend the three minutes of injury time defending both goals. Somehow they succeeded, and the game went into extra-time, where Barbados scored the Golden Goal which ensured them a 4-2 win and qualification for the Caribbean Cup.
2. Leicester vs Arsenal (1997/98)
With Arsenal boasting a 2-0 lead at Filbert Street thanks to Dennis Bergkamp’s brilliant brace in August 1997, the Gunners looked to be cruising towards another three points with less than 10 minutes remaining.
But it merely set up one of the most astonishing finishes to a Premier League game ever.
A late Emile Heskey goal looked a mere consolation for Leicester with six minutes of normal time remaining, only for Matt Elliott’s deflected 93rd-minute effort to level things up. But in the 94th, Bergkamp completed his hat-trick with one of the greatest goals in Premier League history, bringing down David Platt’s looping ball beautifully before bamboozling Elliott and slotting past Kasey Keller.
With Arsenal players pleading for the final whistle, Leicester won a corner in the 96th minute. And, following some head tennis in the Arsenal area, Foxes skipper Steve Walsh pounced to power a header past David Seaman and secure an unlikely draw.