<?xml version="1.0" encoding="utf-8"?>
<android.support.constraint.ConstraintLayout xmlns:android="http://schemas.android.com/apk/res/android"
xmlns:app="http://schemas.android.com/apk/res-auto"
xmlns:tools="http://schemas.android.com/tools"
android:layout_width="match_parent"
android:layout_height="match_parent"
android:descendantFocusability="beforeDescendants"
android:focusableInTouchMode="true"
tools:context=".WorkOrdersList">
<android.support.v7.widget.Toolbar
android:id="@+id/toolbar_actionbar"
android:layout_width="match_parent"
android:layout_height="?android:actionBarSize"
android:background="?attr/colorAccent"
app:layout_constraintStart_toStartOf="parent"
app:layout_constraintEnd_toEndOf="parent"
android:theme="@style/AppTheme.AppBarOverlay"
app:layout_constraintTop_toTopOf="parent" />
<ListView
android:id="@+id/WorkOrdersList"
android:layout_width="match_parent"
android:layout_height="wrap_content"
app:layout_constraintBottom_toBottomOf="parent"
app:layout_constraintEnd_toEndOf="parent"
app:layout_constraintStart_toStartOf="parent"
app:layout_constraintTop_toBottomOf="@+id/toolbar_actionbar"
app:layout_constraintVertical_bias="0.0" />
</android.support.constraint.ConstraintLayout>
match_parent следует использовать 0dp - это значит, что будет использоваться все допустимое пространство, заданное ограничениями
<ListView
android:id="@+id/WorkOrdersList"
android:layout_width="0dp"
android:layout_height="0dp"
...
<android.support.constraint.ConstraintLayout
xmlns:android="http://schemas.android.com/apk/res/android"
xmlns:app="http://schemas.android.com/apk/res-auto"
xmlns:tools="http://schemas.android.com/tools"
android:layout_width="match_parent"
android:layout_height="match_parent">
<TextView
android:id="@+id/OrderFrom"
android:layout_width="match_parent"
android:layout_height="wrap_content"
android:layout_marginStart="8dp"
android:layout_marginTop="8dp"
android:layout_marginEnd="8dp"
android:textSize="22sp"
android:textStyle="bold"
app:layout_constraintEnd_toEndOf="parent"
app:layout_constraintStart_toStartOf="parent"
app:layout_constraintTop_toTopOf="parent" />
<TextView
android:id="@+id/OrderDate"
android:layout_width="match_parent"
android:layout_height="wrap_content"
android:layout_marginStart="16dp"
android:layout_marginTop="8dp"
android:layout_marginEnd="16dp"
app:layout_constraintEnd_toEndOf="parent"
app:layout_constraintStart_toStartOf="parent"
app:layout_constraintTop_toBottomOf="@+id/OrderFrom" />
<TextView
android:id="@+id/DocType"
android:layout_width="match_parent"
android:layout_height="wrap_content"
android:layout_marginStart="16dp"
android:layout_marginTop="8dp"
android:layout_marginEnd="16dp"
app:layout_constraintEnd_toEndOf="parent"
app:layout_constraintStart_toStartOf="parent"
app:layout_constraintTop_toBottomOf="@+id/OrderDate" />
<TextView
android:id="@+id/Applicant"
android:layout_width="match_parent"
android:layout_height="wrap_content"
android:layout_marginStart="16dp"
android:layout_marginTop="8dp"
android:layout_marginEnd="16dp"
app:layout_constraintEnd_toEndOf="parent"
app:layout_constraintStart_toStartOf="parent"
app:layout_constraintTop_toBottomOf="@+id/DocType" />
</android.support.constraint.ConstraintLayout>android:layout_height="match_parent", замените на android:layout_height="wrap_content". В данном случае, вьюха займет пространство, которое хватает для отображения контента внутри ConstraintLayout
<android.support.constraint.ConstraintLayout
xmlns:android="http://schemas.android.com/apk/res/android"
xmlns:app="http://schemas.android.com/apk/res-auto"
xmlns:tools="http://schemas.android.com/tools"
android:layout_width="match_parent"
android:layout_height="match_parent">
<TextView
android:id="@+id/OrderFrom"
android:layout_width="match_parent"
android:layout_height="wrap_content"
android:layout_marginStart="8dp"
android:layout_marginTop="8dp"
android:layout_marginEnd="8dp"
android:textSize="22sp"
android:textStyle="bold"
app:layout_constraintEnd_toEndOf="parent"
app:layout_constraintStart_toStartOf="parent"
app:layout_constraintTop_toTopOf="parent" />
<TextView
android:id="@+id/OrderDate"
android:layout_width="match_parent"
android:layout_height="wrap_content"
android:layout_marginStart="16dp"
android:layout_marginTop="8dp"
android:layout_marginEnd="16dp"
app:layout_constraintEnd_toEndOf="parent"
app:layout_constraintStart_toStartOf="parent"
app:layout_constraintTop_toBottomOf="@+id/OrderFrom" />
<TextView
android:id="@+id/DocType"
android:layout_width="match_parent"
android:layout_height="wrap_content"
android:layout_marginStart="16dp"
android:layout_marginTop="8dp"
android:layout_marginEnd="16dp"
app:layout_constraintEnd_toEndOf="parent"
app:layout_constraintStart_toStartOf="parent"
app:layout_constraintTop_toBottomOf="@+id/OrderDate" />
<TextView
android:id="@+id/Applicant"
android:layout_width="match_parent"
android:layout_height="wrap_content"
android:layout_marginStart="16dp"
android:layout_marginTop="8dp"
android:layout_marginEnd="16dp"
app:layout_constraintEnd_toEndOf="parent"
app:layout_constraintStart_toStartOf="parent"
app:layout_constraintTop_toBottomOf="@+id/DocType" />
</android.support.constraint.ConstraintLayout>

match_parent внутри ConstraintLayout глупо, нужно использовать 0dp, что означает, размер будет ограничен ограничениями, которые вы задали (как бы тавтологично не звучало)
app:layout_constraintTop_toBottomOf="@+id/OrderDate", а должно быть без знака + app:layout_constraintTop_toBottomOf="@id/OrderDate"+ - это создание нового id, он должен быть только там, где задается id вьюхе. И, стало быть, толка от ваших констрейнов нет <?xml version="1.0" encoding="utf-8"?>
<android.support.constraint.ConstraintLayout xmlns:android="http://schemas.android.com/apk/res/android"
xmlns:app="http://schemas.android.com/apk/res-auto"
android:layout_width="match_parent"
android:layout_height="wrap_content">
<TextView
android:id="@+id/OrderFrom"
android:layout_width="0dp"
android:layout_height="wrap_content"
android:layout_marginStart="8dp"
android:layout_marginTop="8dp"
android:layout_marginEnd="8dp"
android:textSize="22sp"
android:textStyle="bold"
app:layout_constraintEnd_toEndOf="parent"
app:layout_constraintStart_toStartOf="parent"
app:layout_constraintTop_toTopOf="parent" />
<TextView
android:id="@+id/OrderDate"
android:layout_width="0dp"
android:layout_height="wrap_content"
android:layout_marginStart="16dp"
android:layout_marginTop="8dp"
android:layout_marginEnd="16dp"
app:layout_constraintEnd_toEndOf="parent"
app:layout_constraintStart_toStartOf="parent"
app:layout_constraintTop_toBottomOf="@id/OrderFrom" />
<TextView
android:id="@+id/DocType"
android:layout_width="0dp"
android:layout_height="wrap_content"
android:layout_marginStart="16dp"
android:layout_marginTop="8dp"
android:layout_marginEnd="16dp"
app:layout_constraintEnd_toEndOf="parent"
app:layout_constraintStart_toStartOf="parent"
app:layout_constraintTop_toBottomOf="@id/OrderDate" />
<TextView
android:id="@+id/Applicant"
android:layout_width="0dp"
android:layout_height="wrap_content"
android:layout_marginStart="16dp"
android:layout_marginTop="8dp"
android:layout_marginEnd="16dp"
app:layout_constraintEnd_toEndOf="parent"
app:layout_constraintStart_toStartOf="parent"
app:layout_constraintTop_toBottomOf="@id/DocType" />
</android.support.constraint.ConstraintLayout>