Not so much as one single point deduction, the major financial difficulties finally out of the way, a popular former player as the manager - this surely had to be United's time. Before the start of the season 2008-09 and the bookies had United down as favourites for the title and many of the United faithful also felt this had to be the season for promotion. McAllister's side had a good pre-season run in winning four and drawing the other three of their seven games. The most notable win came against FCV Dender of Belgium where United won 4-1, two goals from Paul Huntington and one each for Rui Marques and Jermaine Beckford took the spoils in that one.
McAllister was also busy in the transfer market with Andy Robinson coming in on a free, Alan Sheehan made his loan period permanent, Enoch Showunmi came on a free, Robert Snodgrass signed a three year contract and Luciano Becchio signed a three year deal after impressing in the pre-season friendlies while he was on trial. United's start to the league campaign was a little sketchy winning the opening game away at Scunthorpe United 2-1 with goals from Enoch Showunmi and Jermaine Beckford but losing the first game at Elland Road to Oldham Athletic 2-0. A good run in September with United winning all four of their league games pushed them into third place a point behind leaders Oldham Athletic, a position which now mirrored the bookies predictions a little closer. Luciano Becchio scored the only goal of the game away against Cheltenham Town at the beginning of November which saw the Whites move up to second place, a point behind Scunthorpe United but by the end of the same month Leeds had dropped to seventh in the league with dismal defensive
performances largely to blame. An early exit in the FA Cup against non league Histon Town on the 30th November didn't help McAllister and by now fans were sobering up to the possibility that this season might not be as easy as the bookies first led them to believe.
Good news off the field for Leeds United as the club announced a £4.5m profit just three days before their exit in the FA Cup at the hands of Histon. The profits came in a 14th month period that ended on June 30th, 2008, a period which included relegation, administration and a point deduction of 25 points. It was a great turn-around for United's fortunes and fans debated where the money should be spent, the clubs chief executive Shaun Harvey had said in the announcement that the the re-purchase of the Thorp Arch training facility and Elland Road within the next 12 months were a priority but with Leeds' current form many of the faithful thought investment on playing staff, particularly
the defence was paramount.
Not so good back on the pitch with United just picking up 4 points out of a possible 15 in the month of December a run which saw United fall to 9th in the league, now 15 points behind leaders Leicester City and it was enough to see the end of Gary McAllister as Leeds' manager. After the 3-1 defeat at the Stadium:MK against Milton Keynes Dons McAllister was sacked by chairman Ken Bates. Bates didn't waste any time in appointing a new boss for the Whites, Simon Grayson another ex Leeds United player and lifelong fan was persuaded to drop down a division to take on the role. Grayson who at the time was managing Championship side Blackpool was delighted with the move but Blackpool threatened legal action as they rejected Grayson's resignation. The move made Grayson the third Leeds United manager of the year. Grayson's first game in charge was against top of the table Leicester City at Elland Road. The game ended in a 1-1 draw with Robert Snodgrass getting the Leeds goal in front of 33,580 which at the time was the biggest Football League crowd of the season only to be bettered by Leeds again later on in the season. January and February proved to be just above average for Grayson with United winning six of the 10 games and drawing the other four. The last game in that period saw Leeds win at home against Scuntorpe United 3-2 with Jermaine Beckford netting twice for Leeds and Bradley Johnson scoring the other, the win helped Leeds to 6th place in the division and back into a Play Off position. March and April saw even better times for Grayson as he was eventually making his mark on the United outfit. Leeds were only beaten once during
the 12 game period and went on a 11 game unbeaten run which started in late February and only ended with an unlucky 1-0 away defeat at Leicester City on April 13th, with United's opponents scoring in the 92nd minute. The last game in April and Leeds won 1-0 away at Hartlepool United with Jermaine Beckford again delivering the goods. A Play Off place by this time had already been assured but Grayson was pushing his side to finish as high as possible in the league and carry the momentum through the Play off's.
The dispute with Blackpool over the appointment of Simon Grayson finally came to an end in April with The Seasiders settling for an undisclosed fee although it had been reported that the figure was in the region of £200,000.
The final game of the season came at Elland Road on May 2nd, where Leeds took on Northampton Town, It was a comfortable 3-0 win for Leeds with Luciano Becchio, Robert Snodgrass and Jermaine Beckford all scoring for Leeds in front of 34,214, the Football League's highest crowd of the season. That goal by Jermaine Beckford against Northampton took his season total to 34 in all competition's, the best by any Leeds player since John Charles'
record when he scored 43 in the season 1953-54. United moved up one place in the league to fourth as a result which gave Leeds the away advantage in the Play Off's.
Simon Grayson had done a credible job, taking a disjointed United who were in ninth position in December when he took over to finish the term in fourth place and with it a place in the Play Off's.
United faced Millwall in the First Division Play Off Semi final with The Whites playing away in the first leg. A lacklustre Leeds who looked like they would be content with a goalless draw went down 1-0 to a goal which came in the 72nd minute. United had it all to do in the second leg which saw a bumper crowd of 37,036. A dominant Leeds United found it hard to break down a stubborn Millwall defence who were there simply to defend their lead but early in the second half Leeds were awarded a penalty for a foul on Sam Sodje. Up stepped United's top scorer for the season Jermaine Beckford and delivered a tame effort which was easily saved. The pin would have been heard after the penalty miss but for an explosion of celebration in the stands after Luciano Becchio scored moments later. It looked good for United as Leeds compounded their dominance but the equaliser forced Millwall out and in the 74th minute they scored from their first goal threat of the half. Despite Leeds' attack after attack for the remainder of the game there was no way back and for the first time ever United were beat in a Play Off semi.