John Sheridan has signed a centre-half and secured three of last season's Spireites, two of whom were loanees, for the 2019/20 season.
Anthony Gerrard has reunited with his former Carlisle and Oldham boss at the Proact, while Robbie Weir, Josef Yarney and Jack McKay have all signed contracts.
Gerrard, Yarney and McKay have all penned two-year deals.
Thirty-three-year-old Gerrard was released by the Cumbrian side this summer.
He's played 470 league games in a career that includes 140 Championship games and a 2006/07 League Two title with Walsall.
Cardiff City, Hull City, Huddersfield Town and Shrewsbury are also among the defender's former clubs.
His career hasn't been without controversy.
In 2018 Gerrard received a letter of warning from the FA and was told to attend an education course, after a comment made in an Oldham players' WhatsApp group.
Oldham, who sacked the defender, claimed the message related to the Islamic holy month of Ramadan.
Gerrard told the Cumbrian Star in December 2018 he was entering a legal process over his dispute with Oldham, the stress of which had brought on alopecia.
He was initially a transfer target for Town in January, when Sheridan left Carlisle to become Chesterfield boss, but the centre-half signed a six-month deal to remain at Brunton Park.
Midfielder Weir, who has already spent two seasons with Chesterfield, making 63 league starts, has signed a new 12-month deal.
The 30-year-old has worn the captain's armband and Sheridan has spoken in the past of the Northern Irishman's vocal leadership on the pitch.
Yarney was brought in on loan from Newcastle United last season after Sheridan arrived midway through the campaign.
The 21-year-old defender formed part of Sheridan's back three and also featured as a right wing-back.
He started 15 of the 16 National League games for which he was available, adding to 20 League Two games in a loan spell at Morecambe earlier last season.
Yarney was released by Newcastle this summer, allowing Sheridan to snap him up.
And McKay, who came on loan from Cardiff City, has departed the Welsh outfit to become a Spireite once more.
A striker, his first team opportunities were limited.
He made two starts and came off the bench twice, playing 146 minutes of National League action before the end of the season.