Alan Connell scored twice as League Two leaders Bournemouth battled back to end Chesterfield's unbeaten home record and reach the FA Cup second round.
Wade Small centred for Jack Lester to head the home side ahead but Sammy Igoe soon levelled from Liam Feeney's cross.
Connell then forced the ball home after the Spireites failed to clear a corner.
Brett Pitman dummied well for Connell to side-foot in with 15 minutes left, before Chesterfield's Mark Little was sent off for a second bookable offence.
It was the last FA Cup tie to be played at Saltergate, as the Spireites move to a new stadium next summer.
Chesterfield manager John Sheridan told BBC Radio Sheffield:
"Very disappointed in the way we played, we haven't played like that a lot this season.
"I wasn't happy with the goals, I thought we had too many players who were off their game today.
"We just didn't deserve anything from the game, I haven't said that too many times this season."
Bournemouth manager Eddie Howe told BBC Radio Solent:
"We didn't start off fantastically well, but once we got going I thought we passed and moved the ball really well, so it's a really good day for us.
"It was disappointing to concede a poor goal from our high standards but we responded in the best way.
"Regardless of how much money you earn, it's about prestige and wanting to do well and go on a cup run and cause an upset or two."
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