I only want him to win a couple of more matches and get to the 1,000 matches played mark but even that looks less and less likely. Will he ever win another match before he finally calls it quits??
He will get to the 1,000 match mark. This was #999, so if he plays Queen's and Wimbledon, he will end on at least 1,001! Though knowing him, he'll probably lose R1 of Queen's, play Eastbourne because he thinks he needs more matches under his belt before Wimbledon, win a round at Eastbourne, get injured in the second match, and so be unable to play at Wimbledon.
Or, even more Murray-esque, pick up the injury in his R1 Eastbourne win, refuse to withdraw because he thinks he can play through it, exacerbate the injury in the R2 loss, and so have to miss Wimbledon.