A 2-1 reverse in the Czech Republic means England have lost their first European Championship or World Cup qualifying match since October 2009.
Here the PA news agency looks at what else was happening when the Three Lions fell to Ukraine a decade ago.
Ancelotti and Sir Alex fight for title
Eight games into the Premier League season Carlo Ancelotti’s Chelsea topped the table by two points from reigning champions Manchester United, still under the supervision of Sir Alex Ferguson.
The Blues would go on to dethrone United under Ancelotti, winning the league by a single point.
Taio-p of the pops
London-born singer and rapper Taio Cruz topped the UK charts for the first time between September 20 and October 10 with his sixth single ‘Break Your Heart’, while Cheryl Cole and Alexandra Burke also reached number one that month. Elsewhere in entertainment, Disney’s ‘Up’ had just been released and went on to become the 43rd highest grossing film outside the United States and Canada.
Brown winding down
Gordon Brown had entered the last year of his tenure as Prime Minister. Labour performed badly in local and European elections in 2009 and the Scot was heading towards a general election defeat in May 2010 as the Conservatives and Liberal Democrats formed a coalition government.
What’s on the box?
Then London mayor Boris Johnson made a cameo appearance on Eastenders earlier in the month, with the BBC soap later in October announcing that Barbara ‘Peggy Mitchell’ Windsor was to leave in 2010.
Southgate binned by Boro
Last but not least, current England boss Gareth Southgate was in his final days as Middlesbrough manager while Fabio Capello’s Three Lions were losing in Dnipropetrovsk. Boro had made a reasonable start to life in the Championship following relegation but, on October 20, Southgate was dismissed in the wake of a 2-0 win against Derby.