Former Manchester United trainee Sean Geddes was the hero as non-League Worcester City caused the shock of the first round by winning at Coventry.
Geddes opened the scoring from the penalty spot as the Conference North outfit dumped the League One side, winners of the Cup in 1987, out of the competition at the Ricoh Arena.
He popped up again to add a second soon after half-time and although ten-man Coventry netted a late consolation goal, Worcester defied a gap of 64 places in the football pyramid to hold on for a famous victory.
Elsewhere, 2008 winners Portsmouth were held to a 2-2 draw by visiting non-Leaguers Aldershot.