Chesterfield eyeing Middlesbrough giant killing

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Chesterfield midfielder Danny Whitaker is optimistic that his team can take a big scalp in the first round of the League Cup by dumping Championship promotion favourites Middlesbrough out of the competition.

The two sides memorably clashed at the semi-final stage of the FA Cup in 1997 with Middlesbrough progressing to the final after winning a replay 3-0.

Chesterfield are 3/1 to take their revenge and midfielder Whitaker believes it is the style of football of Gordon Strachan’s side that could prove their downfall.

He told Sky Sports: “We do well against the better teams in our league who like to play football – while kick-and-rush is difficult to combat.”

Middlesbrough are 10/11 to win inside 90 minutes, but will have to do so without a number of first-team stars because of a combination of injuries and international call-ups.

Kris Boyd, Barry Robson, Stephen McManus and Kevin Thomson are all on Scotland duty for their friendly against Sweden, while Willo Flood and Gary O’Neil are both sidelined.

Scott McDonald opened the scoring in Middlesbrough’s defeat at home to Ipswich in the first round of Championship games and he is 9/2 to break the deadlock against Chesterfield.

Meanwhile, Jack Lester was on target in the League Two side’s opening-day win against Barnet and can be backed at 6/1 to be the first goalscorer.

Chesterfield have only made it past the opening round of the tournament once in the last seven years. This is their first cup tie at the b2net Stadium, and the match is also televised.

Chesterfield are 8/1 to claim a 1-0 victory and progress to the second round. See the full correct score market here.

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