With his back to the net, Bolland scored on a backhand at 10:25 of the third period to send the Leafs (2-0-1) to victory. Nazem Kadri had the other Toronto goal.
Fredrik Claesson and Andre Petersson replied for the Senators (2-1-0) while Patrick Wiercioch had two assists.
Jonathan Bernier started in goal for the Leafs but was replaced by Drew MacIntyre who played the final two periods. Both were appearing in their second game of the pre-season.
Craig Anderson made his pre-season debut for the Senators and played the opening two periods for the Senators while Nathan Lawson got into his second game of the pre-season by working the final 20 minutes.
The teams entered the third period tied 2-2 following a second period that saw three goals in the final five minutes of the period, including two by the Leafs 19 seconds apart.
While on their second power play of the game, the Leafs finally got on the scoreboard as Kadri beat Anderson at 15:33.
While that goal was being announced, the Leafs took a 2-1 lead as Raymond found the back of the net behind Anderson.
It looked as though the Leafs would head into the second break with the lead but Wiercioch found Petersson cutting into the middle of the ice and the rookie beat MacIntyre with a back hand from the slot.
Claesson scored the only goal of the first period as his slapper from 10-feet inside the blue line somehow eluded Bernier and went in off the crossbar.
The Senators are off until they visit Toronto's Air Canada Centre for a rematch with the Leafs on Tuesday.
Toronto is in Buffalo to play the Sabres on Saturday. The Leafs then host Buffalo on Sunday.