Your first image is out of focus, but it doesn't appear to have any markings on it that might help. Failing that, you may be able to tell which pins are the start and which the ends of the windings as follows, provided you have a suitable signal source of some kind.
Let us ignore the taps in the windings for now and call them 1-5, 2-3 and 6-9.
Pick any winding, say 1-5, and apply a signal to it, say 1V RMS at 1kHz (you need to pick the amplitude and frequency to give reasonable results with your meter whilst not driving the transformer too hard)
Measure and take note of the RMS voltage across 2-3 and 6-9 separately.
Now connect, say, 3 to 6 and measure again between 2 and 9.
If this voltage is the sum of the first two readings then the windings are in phase and you can say 2 and 6 are the starts and 3 and 9 the ends. If the voltage is the difference the the opposite is true. Confirm this by connecting, say, 3 to 9 and measuring between 2 and 6 when you should get the sum.
Note the sum of the voltages may not be quite the same as the combined reading, but if the windings are in anti-phase then it should be considerably less. Also this gives you the relative phase of the two windings not the absolute start and finish of the original winging process.
You can now repeat the test with a different pair of windings, say drive 2-3 and measure 1-5 and 6-9, to get their relative phase. You now have the relative phase of all windings and you can double check by using the last possible combination (drive 6-9, measure 1-5 and 2-3). The ratio of voltages will also give you the turns ratios of the windings.
It is probably safe to say that the taps are in sequence on 6-9, but you can use a similar test to confirm this if there is any doubt.
Note that you appear (from the ratios of the inductances) to be working with a transformer with a fairly high turns ratio, driving the LV side can result in unpleasantly high voltages appearing across the HV side, so take care.