The National League leaders knocked out League One table toppers Portsmouth in round one and are in the midst of a 16-game unbeaten run at the SMH Group Stadium - including 15 wins.
Webb spent nine years with Orient, from 2011 to 2020, and was part of Justin Edinburgh's backroom staff that helped the club back to the Football League.
But even though they are more than holding their own in the third tier following promotion from League Two last season, the 40-year-old believes Paul Cook's Spireites are well positioned to upset the odds once again.
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CRAIG'S BOOSTS
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LENNIE GETS THE LOVE
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ANCHORS A RAPID
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