The city shrievalty existed from c. 1070, early holders of the post including Winebald, Pain, William Gamberell, and Richard Pierrepont. Their status is not easy to assess. In the 1070s Mundræd, a landowner and tenant of the honor of Chester in Cheshire and Suffolk and of Roger de Montgomery in Shropshire, had clearly been a person of consequence. In the 12th century Ranulph I's sheriff, Winebald, had a house in the market place, while Pain (d. by 1178) was evidently a member of a local family with holdings in Chester.
Richard Pierrepont, sheriff c. 1210-15, though not a Cheshire man, had property in both city and county. Pierrepont's standing in Chester is indicated by his obligation to find a doomsman for the city court and by the use of his counterseal to warrant a private deed conveying land in the city. That by then the sheriff was regarded as the earl's principal representative in Chester is apparent from the prominence of Pierrepont and his successor as witnesses of local charters, and from Ranulph III's express mention of the sheriff's office when prohibiting any infringement of a grant of fishing rights to Peter the clerk.
From an early period the sheriff's duties included policing. In the time of Earl Ranulph II, for example, he and the abbot's officials were charged with the arrest and detention of merchants who offended against the regulations governing trading at St. Werburgh's fair. The sheriff probably also, as later, presided over the portmote court, in existence by 1200, when Peter the clerk was exempted from attending it. Almost certainly the portmote represented a continuation of the hundred court of Chester, mentioned in 1086. Apart from the exemption of the castle precincts and St. Werburgh's abbey, probably under Earl Hugh I, the area of its jurisdiction was much the same, though its business may have been modified by the exclusion of the most serious criminal cases, the earl's pleas, known in Ranulph III's time as the pleas of the sword.
In the 13th century the portmote heard all kinds of cases except Crown pleas, though it was especially associated with disputes relating to real estate. Its procedures involved doomsmen (judices or judicatores), who interpreted civic custom and may have been the direct successors of the Anglo-Saxon judges. Responsibility for finding doomsmen rested with particular urban holdings; in the early 13th century, for example, worthies such as Peter the clerk and the sheriff Richard Pierrepont held property which obliged them to provide a doomsman, a duty from which they were exempted by the earl.
By the early 13th century the doomsmen appear to have been well-to-do individuals who attested charters alongside the sheriff. Probably, however, the court remained very much under the influence of the earl. Some indication of how that influence was exercised, and the kind of business with which the court might deal, is given by Ranulph III's charter of liberties granted in the 1190s, which among other things regulated the rights of citizens who bought stolen goods. If a citizen bought goods in open market which a Frenchman or an Englishman afterwards claimed were stolen, he would be quit of action by the earl and his bailiffs upon restoring the goods in question. If a Welshman made a similar claim he had to repay the citizen his purchase price.
The involvement of the earl's representatives in the city's judicial procedures is further implied in the exemption of the citizens from the obligation to obtain leave of the sheriff or the earl's bailiffs before taking surety for the recovery of chattels which they had lent. Though it is not clear whether the sheriff in question was from the city or the county, it seems likely that it was the former in view of his other responsibilities in Chester.