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Fate/Zero vs Fate/Stay Night | Diarmuid vs Cu Chulainn (GRACE)

Cu's Gae Bolg is very dangerous to anyone that doesn't have a rank B or higher Luck stat.

If Diarmuid recognizes Cu's identity and realizes what his spear can do, he might be able to avoid it with EoTM similarly to Emiya Archer in the UBW route. However, that doesn't really accomplish anything for Diarmuid and he will need to get close to Cu at one point or another which increases the likelihood that he gets caught with Gae Bolg.

Diarmuid does seem to be a better combatant when we compare his and Cu's performances against Artoria so he might be able to win if he forces Cu to go into CQC without letting him use his NP. Diarmuid also has a better agility stat than Cu.
Still, Cu's chances to win are higher due to Gae Bolg and Diarmuid needing to get close for a chance to win.
Cu can also just jump back and Yeet Bolg into an anti-army NP and with Disengage as a skill it should allow him to create that gap just fine.
As much as I love Diarmuid, Cu most likely wins. Despite not being as strong, Stay Night's Lancer has better speed (despite stats saying otherwise), due to Archer's statement about Cu's speed. He should also be able to close the gap in strength thanks to Battle Continuation and Gae Bolg.

Diarmuid, while he may have won my heart and has a chance to win under some circumstances, he just isn't emerging out of this sadly. Cu Chulainn takes the W