Here’s my initial answer:
This is a key issue in preaching OT. Many automatically go to the NT, especially from a passage like that. I suppose I would study it in two stages – first what it meant then, then how Matthew / Jesus uses it (raising the issue of whether Jesus was pulling only specific verses or relating to the whole of it by quoting the start of it).
In terms of preaching it, I would probably want to preach it in terms of David first, for a significant chunk of the message, recognizing that everyone else is probably thinking of Jesus. Then going to Jesus and showing his use of it would be perfectly legitimate, thinking about how it applies to us as a text, as well as how Jesus’ application of it applies to us. I preached it a few years ago and found it effective to major on Psalm 22 at 1000BC, with a smaller focus given to Greater Son of David at 32AD, connecting it to us throughout (application of the concept or main idea in reference to David, and response to Jesus in reference to the latter part of the message).
The one thing I would add is that the psalm is not finished 2/3rds of the way through, as some preachers sometimes seem to think. In your study you should probably wrestle with the issue of whether this was a purely predictive text (i.e.not of David, but all of Jesus), a double fulfillment type of text (sensus plenior in some respect – i.e. both of David and of Jesus), or a purely descriptive text that Jesus appropriated as appropriate to his situation and response to it (i.e. all of David, but Jesus could identify). I wouldn’t address all these in the sermon, but I would preach according to my understanding of how the two relate.
There’s a lot to think about with this passage, and I haven’t got into any details here! Hope you can really delight in the study of it.
Hey! Just stumbled upon this – is there a recording available somewhere? I would love to listen to how it turned out!
Sorry, this was a long time ago and I don’t have a recording.