[3] The first leg of Gillingham's semi-final, played at Rochdale's Spotland Stadium on 7 May 2009, finished in a 0–0 draw; BBC Sport commented that "the two sides largely cancelled each other out".

With no further goals being scored in extra time, the semi-final ended in a draw and a penalty shoot-out was required to decide which team would advance to the final.

Daniels saved penalty kicks from Bury's Andy Bishop and Danny Racchi and Shrewsbury won the shoot-out and thus reached the final.

[18] The match was broadcast live in the United Kingdom on the Sky Sports 1 television channel with commentary provided by Garry Birtles and Bill Leslie.

[20] Veteran Nicky Southall, the only member of the Gillingham squad to have played in the club's appearances at the old Wembley in 1999 and 2000,[20] was not included in the starting line-up or among the substitutes.

[22][23] Steve Leslie was not available for selection as he was serving a suspension after being sent off against Bury and both Mike Jackson and David Hibbert had failed to recover from injuries sustained earlier in the season.

[24] After less than a minute, Gillingham defender Barry Fuller was forced to hack the ball clear of his penalty area after confusion among his teammates.

[15][25] Moments later, Fuller challenged Shrewsbury's Ben Davies for the ball in the Gillingham penalty area and appeared to catch him on the upper body with his boot, but the referee did not penalise him for it.

[15][26] Early on, both teams concentrated their attacking play on the left-hand side of the pitch from their respective points of view, with Barcham and Davies featuring prominently in those areas.

[15][27] Shortly afterwards, Gillingham defender Nutter made a long run into an attacking position but his shot rebounded off the back of Shrewsbury's Graham Coughlan.

[15] In the 19th minute, Chadwick was again forcefully challenged by a Gillingham player, this time Simon King, but referee Oliver ruled that no offence had been committed and allowed play to continue.

[15][30] Gillingham gained a corner kick midway through the first half, which reached Josh Wright on the edge of the penalty area, but his shot went high over the crossbar.

[15][38] Shrewsbury's Coughlan was able to close down attacking moves by Gillingham's Dennis Oli and Curtis Weston, leading Sky Sports online reporter Richard Bailey to say that the defender had been "immense" for his team.

[15] With only moments remaining before the half-time break, a Gillingham throw-in was cleared by the Shrewsbury defence but fell to Wright; he hit a hard shot along the ground, but Daniels dived low to his right to make what commentator Leslie called a "really good instinctive save".

[33][39] At half-time the game remained goalless; Paul Fletcher of BBC Sport noted that Gillingham were the better team in the first half and that the Shrewsbury players had looked nervous and struggled to keep possession of the ball.

[15][23] In the 64th minute, Shrewsbury's Kelvin Langmead played the ball to McIntyre, but he was unable to capitalise on what reporter Bailey considered the best opportunity of the game and his header went wide of the target.

[15][23] Shrewsbury continued to apply pressure; Gillingham's King cut out a pass from Ashton to Chadwick and Davies had a shot saved by Royce and shortly afterwards was tackled by Richards when in an attacking position.

[15] In the final minute of the game, Barcham tussled with a Shrewsbury defender; the ball went out of play and the referee awarded a corner kick to Gillingham.

[33][49] Shrewsbury launched a last-ditch attack in a bid to equalise, and Davies crossed the ball to team captain Coughlan in a potential goalscoring position, but his header went over the crossbar and Gillingham held on to claim victory.

[23][33][50] After the match, Gillingham captain Fuller received the winners' trophy from the guests of honour and the club's players and officials celebrated on the pitch.

[50] Mark Stimson stated that he would need to improve the quality of his playing squad for the subsequent season at the higher level and highlighted the financial benefits of his team's promotion, noting that large crowds would be expected for matches in League One against Leeds United, Norwich City and Southampton.