Bolton's first game after being saved from possible expulsion from the English Football League ended in a third consecutive 5-0 defeat, this time against previously-winless Gillingham.
Backed by nearly 750 vociferous fans in Kent, Wanderers were comfortably beaten as Hearts loanee Olly Lee marked the start of his second spell with the Gills by scoring twice.
Despite this week's takeover from Football Ventures, such is the challenge facing the stricken club – who remain at the foot of the table and still awaiting their first league goal this season – that this was only the third time in history that they have conceded four or more goals in four consecutive matches.
Their starting line-up at Priestfield included four teenagers and only Jack Hobbs, who re-signed this week following the takeover, was above 30 years old.
Brown rounded goalkeeper Jack Bonham but was prevented from tapping in by O'Connor.
Connor Ogilvie put Gillingham ahead from 10 yards before Lee fired home a second, six minutes before half-time.
After the break, Brandon Hanlan tapped in a third before Lee completed his brace from close range.
For Bolton – who started the season with a 12-point deduction after going into administration – their misery was complete when a Max Ehmer cross rebounded into the net off Wanderers teenager Jordan Boon with 14 minutes remaining.