Williamson continued his countdown to the milestone by driving his 700th winner with Cast A Shadow at Addington on Thursday night.
He then went to 701 career wins behind the Brad Mowbray trained The Tin Soldier later in the night.
His career tallies puts him 18 wins behind his brother Nathan's total of 719.
The question of which brother will make it to the 1000 wins mark first is the subject of some good natured banter between the Williamsons.
''I am running him down,'' Matthew quipped
''It was great getting to 700. I am just chipping away and slowly getting towards the 1000.
''And I'm catching Nath - which is the goal - to beat him there.''
The Tin Soldier's win also took Williamson to 80 wins for the current season.
He looks at short odds to run down his previous best tally as an open horseman of 83 wins, set in the 2014-15 season.
''It has been a great season. It should be the best season I have had since being out of the juniors and the second half of it has really kicked on, which is great,'' Williamson said.
It was appropriate the Mowbray stable helped Williamson notch a milestone.
The reinsman has become its fulltime stable driver in recent seasons, which has helped him gain a solid footing and increased his opportunities in Canterbury.
''Brad and Mel have been great and driving their team has been huge this season and it helps their horses are always decent chances.''
''I have also been able to pick up drives from a lot of other stables, too.''
Williamson's bumper season has come in the same term he has started competing against his partner, Charlotte Purvis.
Competing against family is nothing new for the driver and it does not have any effect on his driving.
''It's not really a big deal when you are out there because you are concentrating on what you are doing.''
Williamson's colours have been sighted on two trotters from his father Phil's barn this season that he has shares in.
Winnie McGoogan won at Oamaru earlier this year before going amiss and being retired.
The Commando ran second in his first start recently and looks set for success at Addington on Friday.
Registering his own silks does not mean Williamson has any plans to move into training just yet.
''Down the track I will look to get into it, but not at the moment. I will concentrate on the driving while its going well.''
His red silks with black and gold chequered sash are those of former trainer Dick Prendergast.
''Dad worked for Dick and he and his wife Leonie are good family friends.''
