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The Strava Live Segments feature pretty much does this (not a map, but shows the time ahead or behind as you go through a segment) already. You would have to make the "route" into a "segment", but it can be done.
Thanks for your post. I would encourage you to check out our live segments feature. That feature allows you to race against your own PR or a friend's PR. Find out more about Live segments
Also, check out this blog post where some Strava employees describe how they use the feature to compete with themselves and others.