Highlanders' coach Jamie Joseph has injury concerns of his own with first-five Chris Noakes hobbling off the field with an ankle injury.
The visitors were the first to get points on the board after the home side were pinged in the first maul from the kickoff and Noakes made easy work of the 22m kick near the sideline.
However, the Chiefs soon replied with a Cruden penalty after the home side secured the ball from the kickoff rolled it forward putting pressure on the visitors who cracked infringing at the ruck right in front of their goal post and only 20m out.
Noakes nailed his second penalty right in front of the home side's post when Chiefs' captain Liam Messam was caught offside at the ruck to take the score to 6-3.
But it was the Chiefs who grabbed the first try in the 14th minute, after Hika Elliot found some space on the outside and dashed 20m fed to Cruden who found Richard Kahui who set the ruck. The Chiefs found a rampaging Sonny Bill Williams who was pulled down 5m short. Quick recycled ball gave Masaga some space and he carried three Highlander players over the line next to the posts, for Cruden to convert.
It became a tight tussle for the next 10 minutes, then Fritz Lee flopped on top of an attacking Highlander and Noakes made easy work of the penalty in front of the posts and 10m out to take the score to 10-9 to the Chiefs.
The Chiefs spent the next four minutes defending a Highlanders onslaught and were rewarded for their efforts when they turned the ball over and worked it back up the field. Cruden then decided to take the aerial route with a charging Masaga smashing Highlanders fullback Ben Smith to gain a penalty 40m out for Cruden to put it between the posts to extend the lead to 13-9.
After some slick offloads from Sonny Bill Williams and quick plays of the ball from the forwards, Cruden was soon in action again with the boot when the Highlanders were caught offside 10m. The penalty goal would mean the home side would go into the break 16-9.
With the loss of Afeaki in the first half with a suspected broken arm, the Chiefs looked under pressure at times in the scrum. There was no better example than the Chiefs' kick off after the break. The ball was knocked on by the Highlanders but in the resulting scrum the home side were pushed off the ball.
But the Chiefs dug deep and looked to keep the ball away from that particular set play, opting instead to pick and go and spin the ball through the hands.
Highlanders' halfback Jimmy Cowan was replaced early by Aaron Smith and shortly after this the Chiefs were the first to score again from a Cruden penalty 10 minutes into the spell.
At the 15-minute mark Masaga went down with what appeared to be a possible season-ending knee injury and was soon joined by halfback Leonard who came off hobbling and distressed.
The injuries appeared to rattle the Chiefs and the visitors were in for their first try to replacement halfback Smith and for Noakes to convert to bring the score to 19-16 to the Chiefs.
The Highlanders took the lead about 10 minutes from full time, after J Rutledge charged down and re-gathered a Cruden clearing kick. He passed it on to Burleigh who sprinted the 15m to score in the corner and for Noakes to convert to go 23-19.
At the 68 minute mark the Chiefs turned down a kick at goal and went for a lineout play. However, they were eventually repelled by strong defence.
In the 74th minute replacement prop Toby Smith was replaced which meant scrums reverted to golden oldies rules, as the Chiefs did not have a proper front row.
Chiefs 19 (Lelia Masaga try; Aaron Cruden 4 pens, 1 con) Highlanders 23 (Aaron Smith, Phil Burleigh, tries; Chris Noakes 3 pens, 2 con). Halftime: 16-9.
Senior sports reporter Greg Taipari rates the Chiefs starting XV
15. Robbie Robinson: Solid at the back, didn't get many opportunities. 5.5
14. Lelia Masaga: Prior to injury looked dangerous on attack and defence. 7
13. Richard Kahui: A big player and big defender. 6.5
12. Sonny Bill Williams: Worked hard with some classic SBW offloads. 6.5
11. Tim Nanai-Williams: Slippery on attack but didn't get many opportunities. 5.5
10. Aaron Cruden: Despite kick charge down was easily the best Chiefs player. 8
9. Brendon Leonard: Sniping around the ruck, distributed well. 5
8. Fritz Lee: Didn't get many chances off the back of the scrum. 5
7. Sam Cane: Worked hard at the breakdown, solid performance. 5.5
6. Liam Messam: Sets high standards so won't be happy with his performance. 5
5. Brodie Retallick: Locked on to a loose ball which lead to Chiefs' only try. 5
4. Craig Clarke: Quiet night, will be concerned with lineout turnovers. 5
3. Ben Afeaki: Broken arm early so wasn't rated. n/a
2. Hika Elliot: The shining light in a pack which was outmuscled. b
1. Arizona Taumalolo: Scrummaged well but will be looking for more consistency in that area. 5