The much more pertinent question is why was 1C92 delayed on the 12th. Doesn’t matter how many times the valid itinerary vs invalid itinerary wheel is spun it amounts to nought if the delay is out with the control of the industry.
If it was a delay “inside” the tenor of the industry’s control; then I concur with Yorkie in that a claim for 40 mins or so Delay would be valid - with the caveat that as the delayed service (the 1803 PAD -PNZ) was a HSS division service GWR May well deem HSS compensation rules apply; which start at 60 minutes unless I’m mistaken.
To answer the OP’s original question (again). If the reason for the delay is within industry control, then yes it is worth claiming - I don’t think they’ll care that you caught an ever-so-slightly earlier train from Paddington. It’s then up to you whether you think the compensation on offer is enough for you to argue your case if they decline it.
I am broadly in agreement with this. To confirm, 1C92 was delayed by sub-threshold minutes, so deemed within the industry's control. Despite not having the relevant sections of the BR handbook with me, I highly doubt Newbury Racecourse would be classed as an HSS station. Each station would have a classification (sometimes dual) which would determine the service group the journey falls into. The classification of an intermediate station, in this case Newbury, would play no part in this process, even though it may be different.
To address some of the other points raised in the thread, firstly, there is no "should" or "shouldn't" on catching an earlier service than the recommended itinerary, provided that it is not a leg with mandatory reservation. The customer is fully entitled to catch an earlier service if they could make it, obeying time restrictions applicable to the fare paid. It is an absurd notion that the customer must unduly delay himself in order to catch the service on his itinerary in these cases, and completely against the spirit of the compensation regime. This would not apply if the earlier service had no valid connection for an earlier or equivalent arrival time at the destination, in which case it would be deemed that the customer voluntarily delayed himself.
By catching an earlier service, the customer acted reasonably and in good faith by maximising the probability of arriving at his destination on time, so shall not be penalised in the event the railway screwed things up. The argument that they would not have been delayed, with hindsight, had they delayed themselves unnecessarily for the recommended connecting train is a complete red-herring. They were not to know that at the time of arriving at their connecting station.
As for arguments about whether the customer told the truth regarding whether an extended wait was experienced in the case of missing a short-distance connection, it is not for the railway to second guess what the customer may or may not have done. If there were concrete proof that the customer were claiming fraudulently (and I have caught a few in my job, some patently copying information blindly from open data sites), appropriate actions can be taken, otherwise they are contracted to be conveyed to their destination and their words must be taken in having travelled accordingly.
