One of the most helpful resources I’ve encountered in years of intermittent reading is this faculty forum on Christology in the OT at Southern Seminary. Moderated by Tom Schreiner, panelists include Duane Garrett, Peter Gentry and Jim Hamilton.
The central point that all three panelists seem to affirm is that we need to follow the exegetical approach of Jesus and the Apostles, but following Jesus and the Apostles doesn’t mean we abandon grammatical-historical exegesis. Jim Hamilton passes on a foundational perspective when he says:
John Sailhamer is correct when he argues that the OT is a Messianic document written from a Messianic perspective in order to provoke and sustain a Messianic hope.The primary bone of contention in the panel is typology. Peter Gentry actually critiques Grahame Goldsworthy, an author who’s currently influential in Reformed circles. Gentry contends that it’s insufficient to say that everything is typological of Christ. If everything is typological, nothing is. Luke 24 “doesn’t say that every passage in the OT speaks about Christ,” Gentry argues, “but that everything written about him in the law, prophets, and writings must be fulfilled.”
The panelists participate in a nuanced, thought-provoking discussion of the parameters of OT typology. Gentry offers the criteria of correspondence, rooted in history, demonstrating escalation, with a biblical warrant for a typological reading in the context. For a fuller explanation of those criteria, you'll need to listen. Maybe twice.
I would recommend this resource about as much as any I’ve ever encountered. It doesn’t say everything about the topic, but I think you’ll have the opportunity to observe a productive clash of ideas in a pretty short period of time.
The participants refer to a couple resources that develop the concepts in greater depth: Richard Davidson’s Typology in Scripture and S. Lewis Johnson’s The Old Testament in the New.
To those I’ll add John Sailhamer’s Pentateuch as Narrative. Behind this intimidating title you’ll find an accessible commentary on the one coherent book that OT Israelites understood Genesis through Deuteronomy to be. To Sailhamer, the OT is not a semi-random collection of old stories intended to instruct our morality. Instead, He exposes a variety of strategies that the author employed (under the inspiration of the Holy Spirit) to communicate a theological message. And that theological message is a Christological message.
P.S. Andy Naselli just posted a discussion of related matters from Doug Moo.