Dinner plans fell through and we needed food for the family. Called and delivery was promised in 35 minutes, ordered 1 large cheese and a small veggie pizzas, a canzone and Cesar salad. Arrived in 20 minutes! The crust was a little thick on the pizzas but the family loved them. The calzone (small) was perfect for a hungry adult and salad was fresh and dressing was well recieved. We plan on exploring more food options in the future. read more

have been going there since it opened . Love all the food they made! This time my pizza crust was very thin, garlic for days in the sauce! i was sick for 3 days. its too bad because i loved this place. i am tentative to go back! read more

Been coming here a long time, Reliable. Affordable delivery, Love the brother's own pizza. Never really had any problems.

Decided to re-try Checkmate after many years since our local pizza favorite ( Wrox- Christos) had closed. Must be under new or changed ownership since the checkmate of many years ago had always served great pies- very similar in quality and manner to that of Christos.. Was disappointed in the two large pie products -products that lacked even a basic sufficient level of "cheese " and the add-ons. Crust not at all worthy of being rate-able. Dave Portnoy would probably give it a 0. One large half pepperoni and cheeze and one large Buffalo chicken - they also forgot to supply the little blue cheeze container and there was hardly any chicken whatsover at all on that pie. $42.00 and that was with just pickup( without tip) . I don't like that even with pickup they default a 10% tip into the pricing at order time for a product and service that has not yet proven itself. Tips for pickup orders are based on overall EXPERIENCE and product and should not be collected , built into, or suggested at ORDER time. If the service and product was good and a loyal customer then yes no problem with an upfront tip. Not new customers attempting to gain comfifdence in the product/ business. Would always pre- tip the Christos folks. These pie products were a dissapointment and therefore it is the last $42.00 I will ever spend there. Next time I will either order from the Pleasant( they don't have Buffalo chicken pizza ) or take the extra 45 minutes and drive to Town Spa in Stoughton which is amazingly great pizza. read more

Food is great and delivered very fast. The app I used messed up the order and checkmate made it right. Great place.

I love Checkmates and supporting local but if the charge is $2.25 PER topping, then I expect slightly better coverage and quality re: toppings. Second time I'm disappointed; 1-2 pepperoni per pizza slice and mushrooms and onions are barely present and burnt/dried out. read more

Checkmate Cafe - Pepperoni, mushroom and onion pizza. - Pizza Near Me - Roslindale, Massachusetts

Buyer beware: Bad customer service and really subpar pizza! Tonight we order two small pizza and wings through the slice app. One of the pizza was "the pepperoni and a pepsi" special. On both the restaurant website and the slice app, you can choose a second topping at no cost -- we added mushroom. The order came on time but we received a mushroom pizza and no pepsi. The food was also cold for the restaurant to be just 10 mins away. I called the restaurant directly about the missing pepsi before actually checking the pizzas. When I called back and explained that the pizza was wrong, the person on the line responded that the pizza order was for a mushroom pizza. ...Who wants a mushroom pizza when the order called for PEPPERONI?!?!... The kicker: They included a HANDWRITTEN order slip - "sm RONI - pepsi" and the slice receipt is very clear -- see photos. The conclusion: Slice won't provide a refund because the restaurant refused to authorize it. Safe to say I won't be using slice or recommending this place to anyone. read more

See all

I've been ordering from Checkmate for over 20 years. I love their Fried Shrimp Dinner!...and their pizza is, hands down the BEST pizza around!..Best cheese and is melt in your mouth heaven. Bob and Manny are the best and the delivery guy (I call him Georgie) is a sheer delight..you wint be disappointed! read more

Checkmate has always been my go to when ordering subs. Tonight ordered a steak and cheese and the sub wasn't even half filled. Very poor excuse of a sub. Needless to say won't be going back. read more

Checkmate Cafe - Steam and Cheese Sub - Pizza Near Me - Roslindale, Massachusetts

I ordered from Checkmate for many many years. Sadly the quality really changed dramatically a few years ago. I ordered 3 different times hoping it was temporary. It started with the crust which was soggy, not of the caliber expected of them, the ingredients scarce, including the cheese, which never was the case. We were quite regular customers but no more. I miss them as I've yet to find a replacement! read more

Over the summer I ordered food from here for my Husband and I who were doing some work on our place. We ordered about $30.00 and asked for delivery. When the delivery guy got here I handed him $3.00 he seemed upset and looked at me and said "that's it?" I said yeah you guys are like 6 streets from here it's not like you drove for miles to bring the food, then he stomped off and burned off when he drove away. I will not order food from here again. read more

Props for online ordering and quick delivery. Pizza is Greek-style, without a ton of toppings- not bad, although not amazing. I've had better fries, and the 'salad' that comes with an entree is nothing more than shredded lettuce (not even an olive or two?), but their grilled chicken is tasty and not overly dried out, and their menu is pretty large and caters to whatever you're craving. Overall, not bad. read more

I had to try the pizza out of curiosity. Horrifically odd pizza turns this spot into a destination pizza spot to try at least one time. If you are looking for a mom and pop joint trying to imitate "authentic" frozen pizza or Domino's then this place is it! Terrifically bad pizza that instantly makes you think they reheated a slice of Ellios for you. If only I could be in my PJs and could pull a can of Miller lite from the fridge quick enough to get back to my TV in the living room I would be in my mode. read more

The food is good but the DELIVERY DRIVER hits on women (my female friends have shared uncomfortable exchanges with him) and argues about tip. Sadly not going to be ordering from Checkmate anymore. I wish they would find a new driver. read more

I will never order from this place again. They delivered a pizza with a slice missing from it. Oh yeah and it only took 2 hours to get here.... read more

Checkmate Cafe - Pizza Near Me - Roslindale, Massachusetts

I live maybe a mile away. I ordered delivery because I did not have the time to pick it up. Pizza and fries took about an hour and fifteen minutes to arrive. This was after multiple calls by my wife to the place asking where our food was. When the driver arrived. He apologized for being so late. As I received the food and closed the door he asked me about a tip. I replied with a "No" and left it as that. In short, if I wanted lukewarm whatever pizza and fries, I could have just made it myself. It at least would have arrived at a reasonable time. You have been added to my shit list. If it makes you feel better, Stash's is on it too. read more

We ordered a large Pollo. Last month we ordered a small size and got an AMAZING pizza. Nice taste and lots of chicken. This time we decided to go big with a large and dissappointment galore. The picture is attached.Its a 15 dollar pizza and has sparse chicken and broccoli. We expected more. Also it seems other have noticed the same . May be its a cost reduction issue but it impacts customer selection. There are too many places to call for a pizza . read more

Checkmate Cafe - Pizza Near Me - Roslindale, Massachusetts

Really solid neighborhood place for pizza, wings, subs; quick, never messed up an order and the service is always friendly.

Fries were perfect. Crispy just like I like them, and a big serving (enough for at least 3 to share). The cheesesteak could use some more meat but it was tasty (the medium cheesesteak belongs on the small bread). I wish they used rolls instead of long rolls cut into smaller pieces of bread. I hear they are very light on pizza toppings but we didn't get pizza. read more

Tried this place for the first time recently , I got a large cheese pizza and it was by far one of the worst pizzas I have ever had! Two other ppl with me agreed none of us even finished a slice it was that bad and ended up getting thrown in the trash , what a waste of money , if you cannot make decent pizza then it should not be on your menu! Oh and I also got a steak and cheese sub which was also terrible if you want good pizza or a good sub don't waste your time and money coming to this place baddddd pizza . read more

Stopped by with my mom for a quick bite . We ordered the wing ding plate and a cheeseburger. Now, my reason for giving this place 4 stars is mainly for the wing ding plate. I loved the fries and the wings were delicious! I really enjoyed the wings with the sweet and sour dipping sauce in addition to the yummy cole slaw that comes with meal. With that said, this is my new favorite spot for a good wing ding plate. However, I cannot say the same for my burger, they used a big dry untoasted bulkie roll that was bigger than burger patty, so it was very dry and unpleasant to bite into and chew. The bun ended up overpowering the whole meal, how is that even possible? Also, according to previous reviews, most people mentioned how stingy they can be with toppings- not hard to believe since I had to get up twice in the middle of my meal to ask for packets of ketchup until they finally handed over the hidden bottle of ketchup that was behind the counter. So it sounds like they need to cough up a little more of their condiments and ingredients that their food seems to lack and lay off the penny pinching since it's actually doing the total opposite-costing you customers! read more

Only place I'll get a buffalo chicken calzone. They're the best. Love it! Try it if only for that.

My favorite pizza and subs in the area and I have tried all over! Particularly like the cheese pizza and the chicken Parm subs. Friendly quick service. read more

Best chicken gyro around! Love the tzatziki & the owner is so nice. Have been coming here for years.

BBQ Chicken onions Calzone. No BBQ. NO ONIONS. unreal. For the price of this this is ridiculous. NEVER GOING HERE AGAIN. read more

Checkmate Cafe - a half eaten sandwich and a fork - Pizza Near Me - Roslindale, Massachusetts

Let me start with this: generally we really enjoy the food from Checkmate. I love their buffalo chicken salad!! However, I have noticed that sometimes they are WAY to stingy with their toppings. A few days ago we ordered a Large Bacon Pizza- what we got was a cheese pizza with a small bacon decor on it. Tonight, we thus ordered a Large Bacon Pizza with EXTRA bacon. We received a little more bacon pieces on our cheese pizza. Now, it's a perfectly delicious cheese pizza (which is why you get 2 stars), BUT don't tell me you make bacon pizzas, when all you do is merely sprinkle some chopped bacon on it, especially when we ordered EXTRA. So no, just no. Your large "bacon" pizza is a fail. From now on I think I'll justget a large cheese pizza from you and add my own bacon. read more

Not. Bad. Not bad at all, Mr. Bond... However, CHECKMATE, MOTHER FUCKER! ?? No idea behind the name. So anyway, this is that kind of place with pizza, calzones, burgers, hot and cold subs, appetizers, chicken parm, gyros, etc. One of "those" places in the "That kind of place" category. Fuck it, whatever. It's pretty decent. The prices are pretty reasonable. I think the burgers are like $4. Gyros are $5.75 or some shit. Anyway, I've only ever done delivery service, and it's always been 30-35 minutes as advertised. No bullshit. And they're open on Sunday. So, I've had the pizza and the gyros. Both decent. Not awesome, but good. The stars are more for the service than anything. CHECKMATE, MOTHER FUCKER!!! read more

This is my local pizza joint. What good stuff they have! Though it's not fast food at all. The subs are perfectly made and everything is fresh. My friend ordered the steak & cheese and said it was the best he'd had in the Rozzie/JP area. Good service, always with a smile. read more

I'm so sad. This was #1 place where I would go for a great pizza. They recently change ownership and the quality of the food went down. I ordered large cheese pizza and it was tasteless I'd did like anything about it. Very disappointed. Same goes for steak and cheese. Meat was very dry and had no flavor. Somebody have to show them how to use even basic spices like salt and pepper. read more

I'm lukewarm. On one hand, standard pizza place. On the other, they ARE right around the corner. Wouldn't say their pizza is the best, but not the worst either. I do like that their eggplant parm subs are very eatable and not overflowing with marinara. And they don't use meat sauce by default, which, as a former vegetarian, I continue to appreciate. Overall, not really that cheap, not that great, and not that much variety. Sorry, Checkmate. Your name confuses me, and I love and hate you in equal measure. read more

ordered two large steak & cheese subs they were HORRIBLE will NEVER GO THERE AGAIN!!! the subs had no cheese & the steak was like tiny bits of ground meat. when we called to ask they said the cheese was melted inside the steak-rather than give a credit they tried to convince us that it was there we just couldnt see it & thats how they make a steak & cheese-basically it was just bread with no steak and no cheese! my family and i have been customers for years but not anymore! read more

I really like their gourmet pizzas, especially the brother's own pizza w/spinach, chicken, olives, white sauce and the broccoli poppers mmmmmm. Plus free delivery! Just don't get plain pizza, very dull and bland. read more

Best place in Boston for anything Italian. Gyros are awesome!!!! Steak sandwich, pasta, man everything is. Good here. You can't come/live in Boston without coming to eat here. Employes are very nice and relational as well. Love this place. read more

Checkmate Cafe - Ordering counter. - Pizza Near Me - Roslindale, Massachusetts

Checkmate is the best restaurant in the neighborhood. I've been ordering from them for years and I'm finding new and delicious meals. you can never go wrong with a Mushroom, Onion, and Pepperoni, or M.O.P for short or everything with Buffalo Chicken! If you can't make up your mind then you can always trust the person who answers the phone! Fast Delivery! read more

Checkmate has always been my favorite place to get pizza. The pizza is absolutely amazing. Last night my fiancé and I were ordering delivery and saw that they had a pizza burger. Two of my favorite foods combined. Could this be?? I normally stick to one thing on the menu but I thought I'd tried it. Amazing! It's my new favorite meal on the menu. I'm obsessed. read more

Checkmate Cafe - Pizza Burger - Pizza Near Me - Roslindale, Massachusetts

I have been going to the Checkmate Café , off and on for 10 years. I no longer live in Rozzie, but still work in Boston. I stopped in today for a simple boring sub. I took my pricing info from the very large menu board over the counter(with removable letters and numbers) It ended up costing me $13.00. When I asked why, The employee cheerfully stated that "oh those are the old prices" I promptly told him that he can't do that, it's "bait & switch"! He smiled, I took the sub because I was starving. He tried to give me a menu, I tossed it on the counter and said "I won't be needing that". ..And so ends my relationship, in any way, with the checkmate café....(music swells..) read more

Delicious pizza, very fair pricing, quick turnaround. This is my go-to pickup spot (so I can't weigh in about delivery). Really appreciate having a neighborhood joint I can count on. read more

I highly recommend the prosciutto and mozzarella sub! Very tasty and reasonably priced!

I've always been impressed with the food and value! Their salads are very generous with fresh ingredients. They also have very tasty and fresh deserts. I get the Tiramisu almost every time. read more

This 4/5 is judged out of local spots. Checkmate is consistent, timely with orders, and delivers the same solid pizza anytime. The walk-in slices are very good too. read more