There are a few things that can be happening.  Can you post a link to your activity and the segments you are referring to?  

Sometimes, you may be faster than others over the length of a longer segment, but someone else may have been faster for a portion of it.  For example, one person may start fast and then slow down, so they may hold the KOM for a shorter segment near the start, but you may be faster over the longer distance.  Same idea with your various attempts.  You may have done a previous ride that was faster for that shorter segment and either slowed down on other sections leading to a longer total time on the longer segment or you turned off or stopped before completing the longer segment.  

1 is called "Swooping down to the red house " other is " Hopsa hej " . Swooping is longer and hopsa is in the same segment but shorter. 

I looked at your ride done on Sunday, I guess that's the one we're talking about.  I believe that you mistakenly think that both segments end at the exact same point... they don't.  You can verify this by going  each segment's page and then zooming in with the plus sign.  Your KOM segment (Swooping) ends before Tipper Road, Hopsa ends on Tipper just west of the intersection.  Now on your activity page, the Hopsa-hej analysis shows you slowed down hugely at the very end before you finished that segment --  your speed dropped from 31mph to 2.9 mph just before the end.  That's not going to get you a KOM.    
When I was going for KOM's I would always ride like hell for 90 or 100 feet after I thought the segment had ended ----    just to be sure !!   Good luck next time!   

Ignore my previous post if it even made it onto the system -- it contained a few typos - here’s the revised edition: 

I looked at your ride done on Sunday, I guess that's the one we're talking about.  I believe that you mistakenly think that both segments end at the exact same point... they don't.  You can verify this by going  each segment's page and then zooming in with the plus sign.  Your KOM segment (Swooping) ends before Tipper Road, "Hopsa" ends on Tipper just west of the intersection.  Now on your activity page, the "Hopsa-hej" analysis shows you slowed down hugely at the very end before you finished that segment --  your speed dropped from 31mph to 2.9 mph just before the end.  That's not going to get you a KOM.    

When I was going for KOM's I would always ride like heck for 90 or 100 feet after I thought the segment had ended ----    just to be sure !!   Good luck next time! 

If ​@anchskier comes in with a better answer, go with his, he’s actually more experienced at this. 

My reasoning on it is other riders who got positions on both leader boards with only 1 pass on the road on the same date . Ah I'll take it next weekend  if its dry .  Thanks all for the info safe riding !!

​@Tony w - They probably did it in one pass by not slowing down nearly as much.  Also, of note, when I looked at your most recent activity, the GPS tracking jumped around a bit there.  There may have been a bit of a weak signal so it did not get data like it normally would.  It jumps through about 10 seconds in there with only a couple data points.  

What you are seeing is the result of a very poorly created segment.  Segments should not start or end right in/at an intersection, they should be a short distance before or after so stopping or other issues at an intersection don’t interfere with the segment timing.  Comparing your ride with the current KOM holder, it looks like the last point on their track that counted on the segment was just prior to them turning while yours included a point after the turn.  Thier’s allowed them to be timing when they still had speed coming down while yours included both the GPS anomaly and your having to negotiate the full turn.  

It is poorly layed out , that's why I nearly went through the fence at the end .  Thanks again all.