Just about edges him, but that's it.
Let's see:
AO: I think Roddick had more high-level performances here (between the 2003, 2004, and 2005 editions of the tournament) but Med's run to the final in 2021 was pretty clean; however, that is his only notable run at the AO. Willing to call this a draw, but if Med throws in another final or even a victory, he might take the edge
IW: Roddick takes this on account of his 2005 and 2010 runs even if those didn't culminate in wins - Med hasn't really done anything at IW
Miami: Roddick by a good distance
Canada: Their achievements are virtually equal here, but I rate Roddick's 2003 win a bit more highly than anything Med has done there
Cincinnati: Med's win in 2019 was a bit better than Roddick's in 2003, but Roddick also has his 2006 title as well as another final so you'd have to favor him here
US Open: Med's win was quite clean (although Roddick put up a phenomenal display of tennis in the 2003 final); however, Roddick also has his 2006 and 2007 runs which were quite respectable and Med has his 2019 final which was pretty decent too (2020 SF was a bit of a mess); ultimately, this comes down to Roddick having three noteworthy runs so I'd give him the edge
Indoor Masters and the WTF: Med sweeps this pretty clearly I think
Med gets the WTF, two Masters, and possibly a Slam
Roddick gets a Slam, possibly another one, and four Masters
I think we should still put Roddick ahead, but Med has some years of his career left in him to make up the difference, especially if he can get in another good run at the AO.