An early drop goal by Danny Brough edged Wakefield ahead by one point before Wigan scored their third try to lead 11–16 going into half time, following a successful conversion by Pat Richards.

Shaun Lunt finished the game off five minutes from full-time with a try that was successfully converted to provide himself with a hat-trick, and to give Huddersfield a comfortable win.

Luke Adamson touched down two minutes from full-time to give a winning margin of 62 in favour of Salford City Reds.

Two tries within ten minutes gave an eight-point advantage to the home side before Thomas Bosc kicked a penalty to reduce the lead to 8–2.

Catalans scored a converted try in the 21st minute to level game, before two tries and a goal for St Helens meant an 18–8 half time scoreline.

This is the final round where home field advantage is given, due to the requirement that all semi-final matches must be played at a neutral venue.

[20] A sunny Friday evening at the JJB Stadium provided host to the round's first match, between the Wigan Warriors and Salford City Reds.

Salford City Redswere victorious in their last three games going into this match, with Wigan hoping to get back to winning ways after a defeat to Warrington at the Halliwell Jones Stadium.

A line break from Gareth Hock gave the home side a six-point lead after two minutes, following a successful conversion from Pat Richards.

Salford City Reds replied nine minutes later with a line break of their own, eventually resulting in a try for Luke Adamson, converted by John Wilshere.

Hock scored another try of his own after 76 minutes, with Richards kicking the conversion to bring his individual total for the match to twenty, booking Wigan's place in the semi-finals for the first time since 2007.

[22] A Lee Briers drop goal in extra-time was all that separated Hull Kingston Rovers and Warrington Wolves at "New" Craven Park on the Saturday in a closely fought game.

The two sides had recent history in the competition, when in 2006, Warrington Wolves were knocked-out by Hull Kingston Rovers, who were then in National League One.

The home side pressed a ten-point advantage with two 53rd and 60th minute tries from Ben Galea and Jake Webster respectively, the latter of which was the only unsuccessful conversion of the match.

A penalty conceded to the side of Warrington Wolves 's left upright was kicked by Hull Kingston Rovers's Dobson three minutes from full-time to force the game into a golden point situation, the score being 24–24 at the final hooter.

A brief lull in the game was ended with another St Helens try after 21 minutes from fullback Paul Wellens, and this was converted by Sean Long.

Huddersfield were fresh from a 48-point winning margin over Wakefield Trinity from the Super League round the week before, whilst Castleford had not won a match during regular time in four games.

Huddersfield again had a try disallowed for a forward pass, before Brett Ferres scored his only try, and two Kirk Dixon goals gave the visitors a 6–14 lead after fifty minutes.

Only nine days after losing their Super League XIV tie at the Halliwell Jones Stadium, Wigan Warriors were drawn against the Warrington Wolves, whilst a repeat of the 2006 Challenge Cup Final was made with St. Helens versus Huddersfield Giants.

Sam Tomkins, in his first season of first-team rugby, started a Wigan fightback as he caught an offload from the right wing by George Carmont before grounding the ball beneath the sticks.

[29] A Francis Meli hat-trick was not enough to extend St Helens' four-year unbeaten run in the Challenge Cup with a victory in Warrington.

Stephen Wild scored the only other try of the first-half following a line break from Kevin Brown, which was converted to give Huddersfield a 4–10 lead.

Huddersfield extended the advantage further, scoring two tries from Leroy Cudjoe and Brown in the first ten minutes of the second half, although Brett Hodgson again missed both.

A strong defensive performance from Huddersfield prevented another St Helens score, and Wild's second try three minutes from full-time gave the Giants a 14-point advantage.

St Helens' solitary try-scorer Meli scored on the wing straight from the kick-off to complete his hat-trick, but there was not enough time for a comeback.

[30] The Carnegie 2009 Challenge Cup Final was played on 29 August, eight rounds and almost eight months after the tournament started in its preliminary stages.