If the Calgary Flames end up on the outside looking in when the 2009-10 NHL playoffs roll around in April, they might look back at a penalty shot and a four-minute power play on March 15 that could've made all the difference.

Instead, the Flames left these chances wanting and saw a game against the eighth-place Detroit Red Wings slip away in the final minutes on Monday, falling 2-1 in a heartbreaker at the Saddledome.

Tomas Holmstrom scored the winner for Detroit with 1:19 to go in the game, tipping a Johan Franzen point shot past Flames goalie Miikka Kiprusoff to break a 1-1 deadlock. 

"It looked like [Franzen] was going to get control of the puck so I just hung around the net. He knows where I am and I was lucky to get my stick on it," said Holmstrom.

Calgary was up 1-0 after the first period thanks to a goal from Craig Conroy, and had a great chance to double the advantage near the end of the second when Curtis Glencross was awarded a penalty shot short-handed.

But he was stopped by Detroit goalie Jimmy Howard, and 40 seconds later Pavel Datsyuk tied the game while the Wings were still on the power play.

Calder candidate

Howard, a Calder Trophy candidate, stopped 22 shots and is 26-15-8 for the season.

"It was unbelievable, guys were getting sticks in the lane, they broke up passes, we collapsed down and didn't really give them much of anything," said Howard.

Early in the third, the Flames were given a big chance to regain the lead with a four-minute power play after Brian Rafalski was called for high-sticking. But Calgary had a lot of difficulty setting up in the attacking zone and managed only two shots as the Wings killed it off.

"You'd like to find ways to get a goal, but also get scoring chances and keep momentum, so that was definitely a missed opportunity," said Flames captain Jarome Iginla.

The team was booed by Saddledome faithful when the power play was over. Calgary is 2-for-23 on the man advantage in its last eight games.

"We need our power-play to capitalize for us. In these games that are so tight it comes down to specialty teams. That's what the difference was tonight too," said Calgary coach Brent Sutter.

Four-point swing

Those chances could've turned the game. Instead it turned into a four-point swing for the Flames, who now see themselves three points behind Detroit for the eighth and final playoff spot in the Western Conference.

The Flames were hoping for a repeat performance after they beat the Red Wings 4-2 at Joe Louis Arena a week ago. But after a four-game winning streak, Calgary has now gone 0-for-2 in a crucial back-to-back on Sunday and Monday.

Take your pick of which one was the more debilitating. On Sunday during a big division matchup in Vancouver the Canucks played Calgary off the ice in the first period, scoring three goals on 20 shots as Kiprusoff was mercifully pulled, and rode out a 3-1 win.

"I hope there's some guys disappointed in there. There better be. We found ways to lose two games here when we need to find ways to win games," said Sutter. "Tonight we had a chance and never made the most of the opportunity. Last night we beat ourselves because we had a brutal first period."

Monday night's loss might get the nod because of what it means for the playoff race.

There's still plenty of time for Calgary (34-26-9) to make up the deficit with both teams having 13 games left to play, but Detroit (34-23-12) has a much easier home stretch.

The Flames play eight of their remaining 13 games on the road, compared to the Wings' six, and faces tougher competition down the stretch.

Both teams end the season series with two regulation wins apiece, and are also tied on total wins.

Kiprusoff made 26 saves overall, his best coming when he stuck out his left pad to rob Drew Miller of a goal nine minutes into the first period.

With files from The Canadian Press