The first day of September brought the close of the transfer window, meaning a busy day for Blues boss David Moyes.
In came French international forward Louis Saha from Manchester United and journeyman goalkeeper Carlo Nash from Wigan Athletic. Then, with minutes to spare ahead of the midnight deadline, came news of a Club-record transfer.
Marouane Fellaini, a 20-year-old, 6ft 4inch, Belgian midfielder had joined Everton from Standard Liege in a £15million deal - eclipsing the £11.25million Moyes had paid for Yakubu 12 months before.
It was the big-money capture the Goodison faithful had been hoping for and, thanks in part to his unmissable hairdo, he would quickly become a terrace hero.
The month's opening fixture meant another trip to a newly-promoted side, Stoke City. Yakubu continued his fine start to the season by netting for the third successive game, and the Blues appeared to be coasting when another Nigerian, Victor Anichebe - back from winning a silver medal at the Beijing Olympics - made it two shortly after the break.
Stoke hit back through Seyi Olofinjana and a Phil Jagielka own goal but, on his comeback from injury, Tim Cahill settled a thrilling encounter with 14 minutes remaining.
Two successive 2-2 draws followed as the Blues were held by Fellaini's former club Standard Liege in the first leg of the Uefa Cup first round and the third of the Premier League's newcomers, Hull City.
The failure to beat the Belgians was of particular frustration as two defensive errors, including a Joseph Yobo own goal, twice allowed the visitors to go ahead. Yakubu and newboy Segundo Castillo salvaged some hope for Moyes' men however.
An early goal from Martin Olsson then saw Everton dumped out of the Carling Cup at Blackburn, on a night when Moyes was left infuriated by his side's performance.
It was poor preparation for the visit of city rivals Liverpool and a second-half double from Fernando Torres meant the Blues ended the second month of the 2008/09 campaign without a home win to their name.
To make things worse Tim Cahill received a questionable red card for a foul on Xabi Alonso, earning himself a three-match ban.