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
Sir Alex Ferguson and Carlo Ancelotti on the touchline in 2009 (Nick Potts/PA)
The Blues would go on to dethrone United under Ancelotti, winning the league by a single point.
Taio-p of the pops
Taio Cruz arriving for the 2009 MOBO awards in Glasgow (Yui Mok/PA)
Brown winding down
Prime Minister Gordon Brown prepares to add a message of thanks to a tribute to British servicemen, watched by his wife Sarah and Conservative Party leader David Cameron, at a VE Day reception in 2009 (Dominic Lipinski/PA)
What’s on the box?
Mayor of London, Boris Johnson, with Peggy Mitchell, played by Barbara Windsor, in the Queen Vic (BBC)
Southgate binned by Boro
Time ran out for Gareth Southgate at Middlesbrough (Martin Rickett/PA)
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