Oldham Athletic was originally scheduled to play their first pre-season friendly versus Belgian First Division side, Cercle Brugge, on 15 July 2008, but the game was cancelled due to disputes between the two clubs.
Oldham included many new transfers in the line-up, as well as Demar Phillips who was on trial from Premier League club Stoke City.
[10] After an impressive 4–0 rout of Cheltenham Town, Oldham was set to face middle-of-the-table Colchester United at Weston Homes Community Stadium.
[11] Oldham dropped to second place in League One following the 2–2 draw to start September, and was again on the road as they faced Tranmere Rovers.
The game was played at a quick pace for most of the day as a total of 10 yellow cards were shown, but Oldham held out for a 1–0 win.
Oldham played a Friday night match versus local rival Stockport County, who sat in 7th place at the time.
Wolves loaned defender Daniel Jones netted in the 36th minute for the Latics, giving the home side a 3–0 lead at the halftime break.
The ball was bogged down in midfielder for second half, as neither side put pressure on goal—letting Swindon wrap up their third home victory of the season.
[20] A Lewis Alessandra assured that Oldham would end October on a high note, as the striker scored his first hat trick in a 3–0 victory over Scunthorpe United.
[21] After struggling through October, Oldham started November at home against Yeovil Town who was coming off consecutive scoreless draws.
Aaron Brown capitalised from a deep free kick, ending his side's goal drought to give the visitors a 1–0 lead.
Oldham was unable to get a ball past goalkeeper Asmir Begović, who secured a 2–0 victory for Yeovil and gave the Latics their first home loss since March 2008.
Oldham had several chances in the first half including a shot by Lee Hughes which was an apparent early goal, though he was flagged by the official for offsides.
James Walker tried to help him side continue the streak as he smashed the ball past Mark Crossley from point-blank range for a 1–0 Southend advantage.
Michael Ricketts, a former Oldham striker, struck back in 23rd minute with a goal before Alex Nicholls gave the visitors a 2–1 advantage.
Oldham started the match quickly when Adam Virgo brought down Chris Taylor in the penalty box, allowing Andy Liddell to convert a spot-kick for a 1–0 Latics advantage in the 9th minute.
However, Steven Thomson slid a ball past the Oldham defence to Glenn Murray who fired a shot into the roof of the net, putting the Seagulls back level at 1–1.
After several comebacks throughout the season, Oldham again showed their intentions when Lee Hughes poked the ball into the opposition's net for a 2–1 halftime lead for Peterborough.
A Leyton Orient goal looked possible when Adam Chambers got a rebound twelve yards out, but the midfielder sent the ball high over the net.
Near the midway point of the second half, Greg Fleming gave Orient a chance to get back on level terms when he fouled Ryan Jarvis in the box.
Terrific play from Carlisle goalkeeper Tim Krul kept Oldham out of goal, despite giving the Latics nineteen corners.
The Robins gained a 2–0 halftime advantage when Lloyd Owusu earned and converted a penalty kick, getting it past the fingertips of Crossley.
A late robins shot from substitute Damian Spencer hit the post at the end of the match, but Oldham held on for a draw—forcing a replay at Boundary Park.
[34] In the replay, an early 22nd minute shot from Lewis Montrose proved enough for Cheltenham to advance to the second round, and knock out Oldham for the fourth time in FA Cup history.
Shortly before the halftime break, Oldham was dealt a blow when Deane Smalley picked up an injury—giving Matthew Wolfenden his first senior appearance of the season.
[37] For their second game, the Latics were once again away—this time to Burnley at Turf Moor, and Greg Fleming made his debut for the club in goal.
Following Lewis Alessandra's miss in "sudden death", Andy Parrish sent Oldham goalkeeper Greg Fleming the wrong way to give Morcambe a victory.