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I am a .NET Developer and in my company we have developed an engine that attributes missions (transport those packages from A to B) to the best matching driver based on simple rules (pickup address, delivery address, driver's address, driver's vehicule caracteristics (max weight, length), distance to travel, package types to transport, etc ...).
This engine tries to make its best to provide to the user with the 3 best matching drivers the transport mission.

We are trying to address this scenario with machine learning (100000+ missions in our database).
We want to answer this questions:
- Who is the best matching driver for this mission?
- What is the matching score for XXX driver for this mission?

As a side note, our pool of drivers is evolving (some drivers are removed while some others are added in our system over time).

I am discovering ML and learning about basic ML algorithms, but I can not find an algorithm that could answer to this question.

I would like to develop with the new (still in preview) Microsoft Framework for .NET developers (ML.NET), or maybe Azure Machine Learning Studio or Azure Machine Learning Service

Our data look like (simplified) :

Drivers :

Name City VehicleMaxWeight VehicleLength ... StreetName, ZipCode, Country, Latitude, Longitude ... 
Pierre Paris 19000Kg 12m
Francois Bordeaux 26000Kg 12m
Guillaume Montpellier 44000Kg 16.50m
Jacques Montpellier 32000Kg 16.50m
Jean Paris 12000Kg 8m
Bernard Montauban 26000Kg 12m 

Transport mission history :

PickupCity DeliveryCity Service TotalWeight TotalLenght DriverAssignment (Distance to PickupCity)
Paris Marseille S1 2000Kg 5m Jean (5km)
Paris Lyon S2 15000Kg 10m Pierre (8km)
Toulouse Lyon S3 5000Kg 5m Bernard (53km)
... ... ... ... ... ... (...)
Lyon Paris S2 3000Kg 3m ????????????????

Or if the first problem cannot be easily addressed, it would be useful to answer to this question :
Which driver can I select to go from Lyon to Paris for service S2, given the following history ?

Transport mission history :

PickupCity DeliveryCity Service DriverAssignment
Paris Marseille S1 Jean 
Paris Lyon S2 Pierre 
Toulouse Lyon S3 Bernard 
... ... ... ... 
Lyon Paris S2 ????????????????

I would try to predict the column

DriverAssignment

Could you please help me find an algorithm for this task ? And maybe how I can implement it in ML.NET or Azure ML Studio / Service ?

Thank you !

If ML is to be used, this can be formulated as a recommendation system problem: given the sequence of the drivers a mission has been matched to before, what drivers should be recommended for the next time this mission comes up again? Both content-based and collaborative filtering recommender systems can be used. If a mission occurs to be all new (no match history), collaborative filtering can still be used.

OR, however, might be a better fit for this problem. The underlying assumption of ML is: the past operation practices (the data you have shared) have been optimal; this is what the ML will learn as good practices and will use subsequently to give future recommendations. Unless reinforcement learning is used, in which case you need to come up with some notion of cumulative reward.