City travelled to Priestfield for the second time in a month having beaten the Gills 2-0 in the first round of the Capital One Cup, but history was not to be repeated.
Gillingham capitalised on a fast start when Adebayo Akinfenwa glanced a giant throw from Charlie Lee past goalkeeper Frank Fielding in the 22nd minute.
But City hit back on the stroke of half-time and grabbed an equaliser through Marvin Elliott, who powered home a trademark header from a pin-point Scott Wagstaff delivery.
City could have easily won it with Nicky Shorey, on debut off the bench, and Sam Baldock both going close, but O'Driscoll remained upbeat despite now no wins in five.
"It's three games unbeaten in all competitions, so you can use statistics whatever way you want. We're a completely new team, a side in transition," said O'Driscoll.
"So it's going to be a difficult season for us, regardless of the club's size. We started very slowly and with all due respect to Gillingham, we just didn't get going.
"It was a little bit too laboured, and then we conceded the goal. When you look at the success Gillingham have had with long throws, you know you've got to be switched on.
"From our point of view it was soft. You've then got to regroup, and to be fair we came strong at the end of the half and got what I felt was a deserved equaliser.
"That gave us an opportunity to reassess at half-time and we had so many chances in the second half. Creating chances is the crucial thing - to score goals you've got to make chances."