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Bob brings a claim in court and makes a statement in one of his filings which was, for whatever reason, inaccurate/wrong. He then makes statements in a subsequent filing that contradict these. Does his first filing’s statements estop him from making the future statements that contradict them?

Does it matter why each of the respective statements were made? How would the conflict be resolved if not through following the earlier statement? And if these statements are made in different (subsequent) cases rather than in the same claim, would the estoppel (if any) still hold?

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It is not estoppel within the context of a single action, but there are practice rules on this topic. Principally, Practice Direction 16, paragraph 9.2, says:

A subsequent statement of case must not contradict or be inconsistent with an earlier one; for example a reply to a defence must not bring in a new claim. Where new matters have come to light a party may seek the court's permission to amend their statement of case.

If Bob had simply made a mistake or had incomplete information then that is different from if he were trying to develop a totally different basis of claim. The court's discretion will be exercised according to the interests of justice, including dealing with cases swiftly and cost-effectively.

The earlier statements are preferenced in this way, which is consistent with the idea that Bob ought to bring his best case up-front. In particular, he is expected to raise all matters in the same action which he possibly could. This is the "Henderson" principle, after Henderson v Henderson (1843) 3 Hare 100.

A related concept is "issue estoppel", which is what you refer to in the final part of the question. If an issue was decided in one set of proceedings, then in a subsequent action between the same litigants it is taken to be already proved. The term is of American origin but the doctrine is older; see "The Duchess of Kingston's Case" (1776) 20 State Trials 355. The Duchess was tried for bigamy in the House of Lords, and sought to introduce an earlier decision of the Consistory Court of London that the first alleged marriage had not taken place. The point of law was referred to a panel of judges who said (at 537ff) that "the judgment of a court of concurrent jurisdiction, directly upon the point, is as a plea, a bar, or as evidence, conclusive, between the same parties". But this was not enough for the Duchess since the criminal trial was not "between the same parties", and the jurisdiction of the ecclesiastical courts was different. She was found guilty but escaped punishment thanks to benefit of clergy.

If some point was raised before the court but not decided, then this does not arise. But the other party could make use of a contradiction as part of their own case.

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