1399 - 1413 King Henry IV .

Granted a pardon to the mayor and citizens for their service to Henry Percy.
In this reign the women appear to have been especially forward in disobedience to the city regulations , going outside the City Walls into the suburbs to meet the country people as they brought their supplies into the city for sale . Thus the wives of Thomas Dod , Richard de Caldecote , Richard Bucstones , Thomas Aleyn , Robert Symesson , Thomas de Torporlowe , William de Bebington , Ac . , bought victuals in the suburbs , two of them have been a brisk business at Handbridge and Broughton and the other approaches to the city . These forestallers were very troublesome and , we may well imagine , abusive to the officers of the city , especially the female traders who were distinctly in the majority . ( Morris Tud & Plan p 403 )

Henry Prince of Wales and earl of Chester , eldest son of Henry IV . confirmed all charters and gave the mayor and all citizens power to hold and enjoy their ancient customs .
All trades were required to bring their wares into some public place as a market ( later into the Common Hall ) , so that their mercantile transactions might come more readily under supervision , and that no citizen should have any advantage over his fellows . An hour was fixed before which no selling could commence . A regulation in the mayoralty of John Hope , Henry V. 1421, forbade butchers , fishmongers , and cooks to buy calves , fresh fish , capons , or hens before the first hour ( ante horam primam, six o' clock ) , or to go outside the city to forestall the same before they were brought into the city ; and they were directed to permit the same to be brought to the market place for sale under penalty of disfranchisement and a fine of 6/8 to the Sheriffs . The same year an order was made that no foreigner ( extrancus ) or baker should buy , or cause to be brought , any grain within the market before eleven o' clock , nor after that hour until the citizens and commonalty of the city were able to buy in sufficiency for themselves . The penalty was imprisonment and 6s 8d .
The Chamberlin of the county palatine obviously had powers and influence in Chester . This office was also held by the Stanleys : Sir William Stanley a brother of Thomas, Lord Stanley . from 1461 - 95 ; by Edward , earl of Derby from 1559 - 65 ; by Henry earl of Derby from 1588 - 93 ; and by William , earl of Derby , The Stanleys of Knowsley and Lathom of West Derby east of Liverpool , became in the fifteenth century the most powerful family in the North West using ' double dealing and unprincipled behaviour ' to accumulate large estates . The title of Derby was conferred on Thomas , Lord Stanley , in 1485 . Chester like other towns in the North West , disliked ' the earls as representatives of a hated outside authority intruding into their affairs ' . ( C.C. C. R.O. Tudor Chester p 16 )
The wardship ( sergeancy ) of the Watergate ( port entrance ) was to belong to the Stanley family , who also had the right of collecting tolls at Chester Fair . This right they proclaimed by blowing a horn at the Gloverstone . Stanley Palace 1591 was the official town residence it has beautiful Elizabethan oak gallery ,
On more melancholy occasions the Sheriff, bailiff , and town clerk rode there to receive condemned criminals from the hands of the constable . The poor wretches were then taken away in a cart to await the time of execution .



1460 The Pentice was rebuilt at the City's expense , this seems to have covered only the southern part as there are references to the rebuilding of the north side in 1497 . There are further references to the enlargement of the Pentice in 1573 . This is probably the structure shown by Randle Holme .

In 1459, Henry VI., with Queen Margaret and her son Edward, visited Chester, and bestowed little silver swans on the Cheshire gentlemen who espoused her cause

Henry VI King of England confirms all the former charters . and that his charter recites what great concourse in times past , as well by strangers as others has been made with merchandize into this city , by reason of the goodness of the port here ; and also what great trading for victuals into , and out of Wales , to the great profit of the city , until the time of that then late rebellion , which should seem to be that of Owen Glendower . And then shewed how the same port of Chester was lamentably , decayed , by reason of the abundance of sands which had choaked the creek ; and for these considerations releasth to the city 10L of the fee farm reserved by Edward I .