Doflamingo wins round 1 with moderate difficulty, round 2 easily
This fight is closer with Luffy being able to use Gear 4th.
Doflamingo would have beat Luffy 1v1 rather easily in dressrosa arc.
Now before anyone jumps on me I'll prove it:
Point 1: doflamingo was critically wounded. Gamma knife was literally a fatal wound. He would have died except for fact he literally stitched his own organs together. There is no way he was even remotely close to 100%.
Point 2: Doflamingo was exhausted. He had to fight law, the town, luffy etc. he got no rest
Point 3: Even more important then him being mortally wounded is fact Doffy when fighting luffy was full on bloodlusted. Doflamingo himself said that his DF was a versatile fruit that specializes at medium to long range. He was literally fighting in a method advantageous to Luffy. 1 he would not have been able to use Colour of Observation, and 2 he could have easily dodged King Kong Gun if he didn't try to out muscle G4 Luffy.
So what does that mean for this fight? Well without G4 Luffy is badly outclassed in physicals so he loses R1, and loses R2 worse as if both bloodlusted he loses his observation which is only real difference from first fight.
To be honest Doffy may be one of the most tiered characters. He beat Law and Luffy while critically wounded. It took an entire country/ alliance to beat a mortally wounded, exhausted and completely insane version of him. I'm not sure Current Luffy could beat him easily, if at all. It's hard to say as his injury came from hax and because of it we never saw his full powers. We know he was not scared of admirals at all and was willing to fight them, he low difficulties WB commanders. The only person he thought he couldn't beat was Kaido, which based on what he did to Luffy is understandable.
Luffy doesn’t have the damage output to put Doffy down without G4.
Cracker bodies him. Even with G4 Luffy wasn’t getting anywhere and still needed help from Nami to moisten the soldiers. Cracker’s power-set is so specific in required counters that he remains the one narratively same tiered enemy Luffy still cannot beat even after his boosts from the arc.