August marked the start of the new season - with a European date.
A week after the final pre-season outing against Udinese at Goodison the Blues faced Spanish outfit Villarreal in the first leg of the club's Champions League qualifier.
The match ended in a narrow 2-1 defeat despite a first-half strike from James Beattie to cancel out the visitors' opener.
But the tie was far from over for the return in Spain in two weeks later.
The Blues responded to an early setback in that game by clawing a goal back from Mikel Arteta and then, controversially, having a second seemingly good goal from Duncan Ferguson ruled out by referee Pierluigi Collina.
Salt was rubbed into the wound for the Blues with a late strike on the break from Diego Forlan as the visitors chased the second goal that would have taken the tie into extra-time.
That run of bad fortune set the tone for what proved a bitterly frustrating month for the Blues.
An opening day Premiership defeat to Manchester United was followed by a battling 1-0 victory at Bolton. But even that was marred, with Alesandro Pistone being ruled out for the remainder of the season just weeks after re-signing for the club because of a knee ligament injury.
The Blues ended the month resigned to competing in the UEFA Cup and on the back of another defeat - this time away to Fulham.
The 1-0 reverse also saw Phil Neville, who had been signed at the start of the month in time to figure in the Villarreal encounters, being dismissed for the first time in his career after picking up two yellow cards.
David Moyes was able to add Matteo Ferrari to his ranks for the trip to the capital after securing the Italian defender on loan until the end of the season from Roma.
Nuno Valente followed in time to beat the transfer deadline, signed from Portuguese side Porto to provide cover for the troublesome left-back slot.
Complications with the ankle problem that had kept Gary Naysmith out of action since April added to the manager's urgency to dip into the transfer market.