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Thanks for your post. Are you familiar with the My Results filter on segment leaderboards? That filter allows you to view your effort times on a given segment, with your best effort at the top sorted in descending order. The date of each effort is also shown, along with other data (for example heart rate) when available.
Yes I am. I'm an aging athlete (65 yrs old) and constantly trying to prove i'm not losing fitness 😉 So knowing when the last time was that I did a swim, run or bike that was as long or fast or powerful helps me gauge how i'm doing. So it's not always segment tied and can be just relative to a workout, And when it is tied to a segment, the ones i'm usually most interested in have been done 50 or more times. Some upwards of a couple of hundred. (I've been an active member since 2012) So it's hard to scroll through and look for the last time I went that fast on a segment, especially on the mobile app.
You can use Best Efforts to track your fastest times (and power outputs on the bike) and compare your current outputs to those.
We don't currently offer best efforts for swim activities, but we have an existing idea submission for it here, and we would welcome your vote and any comments you would like to add.
I would recommend using the "My Results" segment filter on the Web in the scenario when you have a lot of efforts on the segment. On the web, you'll see your best time on that segment at the top of the list of segment efforts, and they'll be listed in descending order from there. That way, it's easy to compare your current time on the segment to your fastest ever time, and view the date you completed that.