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That is because your new ride IS the new baseline.
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If you look at a ride right after it is uploaded, there is a small window to see that the completed ride is above the prior season or all-time record. But in short order, TR runs something and then updates the season or all time info to match the data from your new ride.
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It is confusing at times, because I load some workouts quickly and look right away expecting records. I don’t see any “trophies” for a bit, even if I manually load the the all time or season for comparison on the chart, and see clear indication of new highs.
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But at some time interval I don’t know, TR catches up and then uses the new data as the season or all time value. You will see the trophies and can drill to see the improvement at that time.
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I see that as a minor problem, because you don’t see what the old info was or the delta to your new accomplishment. I get that it is hard since the new value reset the record, but it makes it difficult to find the record and the change you just experienced.
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You are forced to use the “View Details” option, and dig in there.
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Looking at the All Time tab, you can see some of the progression in your season or all time area.
This overall issue is less than ideal (looking at Personal Records) and we have several discussions with feature requests to improve them. Here is the main one: