England had the better of the chances in a tiresome first half with a Kieran Trippier free kick in the 42nd minute whizzing past the goal.
And the England captain might just be the difference maker for the Three Lions.
After a wait of nearly four minutes and clear attempts by Johan Mojica to scuff up the penalty spot, the country's talisman coolly lifted the ball down the middle beyond the dive of Ospina.
Such arrogance on the part of the English may play right into the hands of Colombia, who with the likes of Juan Cuadrado, Juan Fernando Quintero and Radamel Falcao posses the firepower to expose their weaknesses.
Referee Mark Geiger had a night to forget in Moscow, with the American official struggling to regain control of this feisty game after failing to send off Colombia defender Wilmar Barrios for a first-half head butt. England scored four goals from set pieces and two on penalties.
Expected Crowd Turnout: With its last hosting in this FIFA World Cup 208, Spartak Stadium is expected to be a jam-packed affair, as Colombia meet England, with a total crowd attendance of 44,800.
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But Colombia's Espina saved one fron England's Henderson, putting the side 3-2 up, before Uribe hit the crossbar, giving Trippier the chance to equalise, 3-3.
No other country had lost as many penalty shootouts at a World Cup, but when history was against them England's inexperienced team held its nerve to see off Colombia in a penalty shootout and progress to the quarterfinals.
Harry Kane became the first player to score in six consecutive England appearances since Tommy Lawton did so in 1939.
After that, it would be England's first World Cup final since 1966, but there's a long way to go.
It was the most intimidating atmosphere England have experienced so far this World Cup, the players being jeered as they entered the pitch for the warm up.
Tite's Brazil eased to a 2-0 win over Mexico on Monday and are still the favourites to win the World Cup with the bookies. Though Colombia are unsafe without Rodriguez, having their star available would be a huge boost, as the Bayern Munich man was involved in 48 percent of Colombia's goals in qualifying, and added two assists in just 152 minutes so far in Russian Federation.
We expect Colombia to dictate play for at least half the game, with England content to launch repeated and rapid counter-attacks.