A single goal, scored by Leyton Orient's Jabo Ibehre midway through the first half, was enough to send Luton to their fourth defeat on the spin.
A shot-shy Hatters failed to really create much in front of goal, despite dominating proceedings in the second half.
And to make matters worse, Orient's goal came from a sloppy Sol Davis clearance that gifted Ibehre his fifth of the season.
The result means Hatters boss Mick Harford is still searching for his first win as Luton boss.
Luton went into the game handing George Beavan his full Hatters debut after impressing in the loss against Bournemouth last week.
The youngster, who celebrated his 18th birthday on Wednesday, kept Chris Perry out of the side to partner Keith Keane in the centre of defence.
Hatters boss Mick Harford made one other change to the side with Calvin Andrew replacing the injured Darren Currie.
Orient, who included former Hatter Adam Boyd in their starting line, were without influential defender Tamika Mkandawire.
Luton made an encouraging start to the game, as they began in confident fashion and looking comfortable on the ball.
However, despite Luton's bright start it was the visitors who twice came close to taking the lead inside the opening ten minutes.
Firstly, on five minutes, an Adam Chambers cross from the right found the head of the unmarked Ibehre whose effort failed to trouble Dean Brill in the Luton goal.
Then, just four minutes later, Paul Terry's through ball found its way to Stephen Purches whose half volley from the edge of the area almost found its way into the corner of the Hatters net.
The Hatters were looking promising on the attack and on 14 minutes Dean Morgan rolled his marker to fire a shot just wide after a cross from David Bell was flicked on at the near post.
A minute later and Luton were lucky not to have been reduced to ten men when Lewis Emanuel appeared to push his head into the forehead of Jason Demetriou after the Hatters full-back prevented the Orient defender from taking a throw. Strangely, the referee booked Demtriou for his part in the incident.
On 26 minutes, Orient broke the deadlock when some sloppy defending from Sol Davis gifted Ibehre a goal. A cross from the left by Terry found Davis but the full-back's clearance fell straight into the path of Ibehre whose shot from eight yards hit the underside of the crossbar and rebounded into the net.
Orient were soon content on sitting deep in their own half and soaking up any of the Luton pressure, as the Hatters struggled to find that slice of luck in front of goal with Morgan and Sam Parkin both firing efforts well off target.
Orient finished the half the stronger side and almost grabbed a second goal on 42 minutes when Boyd's turn and shot flying straight into the arms of Brill.
AT HALF TIME: LUTON 0 V 1 ORIENT
The visitors almost made the perfect start to the second half when on 53 minutes Demetriou found space on the edge of the area to fire a curling shot which was met by a wonderful save from Brill, diving full stretch to his left.
Luton responded by going close on 59 minutes when a cross from the right was flicked on by Andrew, and headed by Parkin into the path of Matthew Spring whose first time volley flew harmlessly over the crossbar.
The Hatters almost went further behind on 61 minutes when Demetriou's corner was met by a towering header from Samuel Oji but the former Birmingham man was denied when his effort was cleared off the line by Davis.
Luton had their best effort of the game on 78 minutes when Morgan's cross from the right was met at the near post by Furlong's header but his close range effort bounced off the chest of Stuart Nelson in the Orient goal and straight into his arms.
The game ended in ugly scenes when a mass brawl erupted with three minutes to go which saw Steve Robinson and Oji go into the referee's notebook.
AT FULL TIME: LUTON 0 V 1 ORIENT
Luton: Brill, Morgan, Bell (Furlong 68), Parkin, Robinson, Emanuel, Andrew, Keane, Spring, Davis, Beavan
Subs not used: Goodall, Perry, Talbot, Beresford
Bookings: Parkin (69), Emanuel (85), Robinson (89)
Orient: Nelson, Purches, Saah, Chambers, Gray, Oji, Ibehre, Terry, Boyd (Thornton 81), Palmer, Demetriou
Subs not used: Thelwell, Melligan, Corden, Morris
Bookings: Demetriou (15), Gray (74), Oji (88)
Referee: Mr P J Joslin
Attendance: 6,412 (1086 from Orient)
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