Always get the same thing here. Love their fresh Buffalo fingers and good quality blue cheese. It's Greek style pizza but very good if that's the style you like. Most importantly the employees are super nice and always accommodating. read more

Checkmate used to have good food years ago, but what a disappointment it has become. I ordered food from there and first off, they are wayyyy overpriced for their portions and food quality/quantity. Second, I ordered chicken fingers and there was only 3 chicken fingers (shown in picture)!!!! A few other reasons, the chicken wings and French fries were black, It looked like their oil hasn't been changed in a while. I also ordered 3 small pizzas, which were extremely flat and well over priced for the size. There are better pizza restaurants in the area...I wouldn't recommend... read more

Checkmate Cafe - a variety of food items - Pizza Near Me - Roslindale, Massachusetts

ordered delivery twice and while their menu says "free delivery" its not true, they will always add $2 to your bill, so if you dont tip more than that, double check your bill before you pay. other than that, the food is really good. I've had steak kabobs and steak tip dinners as well as pepperoni pizza. I wish the steak would be undercooked, but its delivery and you can't help that. the pizza is pretty tasty, pretty standard as well, nothing spectacular. they also deliver in under 30 mins. will definately order from here again. read more

In Roslindale sifting through delivery menus with no clue as to which is worth calling up? Save your time, thrown out every menu except Checkmate Cafe. These guys make outstanding sandwiches and pizzas. Of note are the steak tip and gyro style sandos and the greek style hawaiian and white sauce with chicken and broc pizzas. Dont ever just pop in if you are hungry b/c you will be waiting, they are always swamped with delivery orders so just go home and have them deliver. They are fast , courteous on the phone and simply the best in Roslindale. Little known fact, if you close enough to them in JP (ie near the Arbs or Washington St) they will deliver to you. read more

Foods good. A little overpriced for the quantity at times. I only live around the corner so delivery is quick when I'm too lazy to leave the house. I went in for a slice of pizza that clearly had been sitting there all day. $2.60+ tax for a slice of hours old cheese pizza. read more

The Buffalo chicken calzone is probably the best calzone I have ever had. The rest if the food is nothing special...

Checkmates makes the BEST calzones around here! There subs and stuff are also good!

Their fish and chips are really yummy and the chicken tenders are the best! Super fast delivery too!

Great pizza and sandwiches. My kids love it. And as a Vegan, I appreciate the pizza they'll make me with no cheese, adding olive oil to enliven the taste! read more

Clean, dependable, fast and friendly. Checkmate is one of the better mom and pop pizza joints in the Roslindale area. The delivery is always on time and the food is never soggy or cold. Their subs are huge and affordable, the pizza is a mix between Greek and Italian style and by that I mean, it's thin like an Italian but tastes like a Greek pizza. I think their turkey club is tops because they actually use real sliced turkey breast, unlike other mom and pops who used that slimy deli stuff. You can count on Checkmate for above average take out that is perfect for a lazy Sunday. read more

Gyros are ok. Not a fan of the pizza at all, but we love the calzones, which are of a size that you can save half for later (they reheat well in the oven). The salads are nothing to write home about. read more

Someone also mentioned the change of ownership and let me tell you, this was my favorite local pizza place and now I'll never go back. When the delivery came, my dogs started going nuts and I told him to hold just a moment while I contain them (didn't want them jumping on him or escaping through my gate, which he had left open). After maybe 30 seconds, I opened the door and the driver was half-way back to his car. Apparently he had no patience for me and was just going to leave. I asked him where he was going and he got super pissed. Seemed like he was ready to fight me. Needless to say, no tip for the dude. I called the restaurant and told them my story, thinking they'd be sympathetic since I've eaten there twice a week for four years. The owner was nice enough and credited me my pizza... which was the right thing to do. An hour later - at 9:30pm - someone rings my doorbell. Of course, dogs go nuts and I certainly wasn't expecting anyone. In fact, I thought the creepy delivery guy was coming back to finish that fight he wanted to start. So, I go out onto my front deck (second floor) and call down to the front door... turns out it's the owner. Making a house call at that hour - in light of the original complaint - was the exact wrong thing to do. I understand that he thought he was doing a nice thing, but I thought it was a little weird and unsolicited. I was actually in the middle of trying to eat the pizza in question when he shows up unexpectedly and interrupts dinner and riles up the dogs. It was when he showed up that I realized the owners had changed and, now that I know, I won't be going back. read more

New to this part of Boston I was very happy to find a new great pizza place to replace my "old faithful". I love their selection of gourmet pizza which is refreshingly different from all the others. They offer all the extras which allows you to create your own, or make substitutions on theirs. I have also had their subs which are also definitely worth getting. A must try is their Fried Broccoli. They are a tasty, more mellow version of a popper. Yet another great way to turn a nutritious veggie into something naughty and delicious. read more

We've been ordering from them for 10 years. We order from them at least once a week. We love the meat lover pizza and the extra cheese pizza. Their fish and chips is good too. We also get chicken wings. They are nice people and straightforward. We were very happy when they added deserts to the menu. My favorite item on the menu is the calzone. read more

Chicken broccoli ziti was watery with no flavor at all. The broccoli cheddar bites are good

Good food and the serving sizes are great. I love their fries and their fish sandwich. I have also tried their pastas, those have been pretty great too! read more

Great place for a quick sub, pizza, or wrap. Great local spot in Roslindale for pick up or delivery.

I will always miss the previous owner. The food and prices were excellent. The food is still decent but not delectable. if you order an italian sub from here, it is a pretty much a flat sandwich. A mere sprinkle of lettuce, tomatoes and onions. I forgot how good an italian sub can be until I went to a different sub shop. They do skimp with some of the sandwiches and pizzas. I still order from there often because at least they show up in a short amount of time and your food is hot. Its not bad at all....its just not the best. This used to be the ONLY place I would get takeout but not anymore. Their wing dings are good though. read more

Checkmate is awesome!!! They have great pizzas especially the gourmet ones and their calzones are the next best thing to making my homemade. They have hot wings and tenders that are killer! The best burger meal deal and I love their onion rings!! My hubby is a huge fan of the steak tip dinner!!( I recommend getting the grilled mushrooms, peppers and onions wit it) The delivery is always when predicted even in bad weather. The folks always no my hubby's voice on the phone which is cool! Nice to know they recognize regulars in person and on LL. read more

I love Checkmate Cafe! I get their veggie pizza- the fried eggplant adds an amazing crunch that you don't expect with most pizza, and usually I don't like thinner crusts, but this crust is to die for. Also, their delivery time is great. Checkmate Cafe needs to work on something, though: CONSISTENCY. I always order the same thing, but I'm never sure what' I'm going to get. Will they forget a topping, like the precious fried eggplant, or even two toppings? Will they put a skimpy amount of black olives or load them on? Will they inexplicably suddenly start putting an overwhelming amount of garlic under the cheese, spread in large clumps throughout the pizza? Who knows. When I've tried to explain it on the phone, whoever answers is in too big of a rush to listen. When they get it right, it's delicious, but I wish I could depend on what I'm paying for. read more

Very good Pizza.We had the Patriots Mykonos, Pollo and The Meatlovers. The best was Pollo and Mykonos and The M.L is always the bomb. The burgers and salads were also prety great. They are very nice and location is also cool. read more

I've got delivery and takeout from checkmate several times and can't say a bad thing about it. Food has always been incredible and delivery has never taken longer than 35 mins. I've ordered from every place in the rozzi and westie areas and this is by far my favorite. Buff chick calzone =A+ read more

let's just say " I miss the old owners". Over-priced food and the burgers are smaller than the bun.

I just got an order from them and their customer service is non-existent. This is the second time I have ordered and both times the delivery guy has did not have a slip and just quoted a price that was different from what was expected. The first time I ordered the driver said he lost the slip and quoted me a price that I called to verify and it was two dollars more. I asked him for the menu they were supposed to include and he said, "It's the same one you have." I told him I was pretty sure this was an older menu and his attitude was like "whatever," and "maybe next time." Again, the driver didn't bring a slip. He asked why we needed it and then went back to his car. There were no individual prices on the slip; just a total scrawled at the bottom. This time the order was like $8 more than the lady who ordered said she was quoted and $5 more than my menu tally. I called to ask about it and the owner (?) was very, VERY rude. he said they never put prices on their slips and when I asked why, he said, "because I just don't. That's why you have a menu." Seriously? How about your driver never gives us a menu even though we ask for it? How about if that is the right menu, your prices STILL don't add up - even after tax? How about Roslindale is inundated with sub shops to the point that we don't have to put up with rude, shady businesses? Too bad because the food was decent and we were thinking Checkmate would be the new go-to spot but now no one here want's to do business with them. Not that they care since he told me he was busy when I complained about his/their attitudes. read more

We order from here about twice a week. The place makes awesome food. I tried every sub shop around Roslindale pretty much and this place is one of the best. Even the Deilvery guys are cool people. Good place for some grub. Enjoy. read more

They have great subs - consistently good for the last 10 years. Its always clean and sunny in the shop - good prices too. 4 stars because their pizza is just ok. The comment that someone made about them having "the best italian food in Boston" is weird and totally absurd. This is a classic greek pizza/sub place done right. read more

Never again will I ever order food from Checkmate Cafe 902 South Street Roslindale Ma 02131. I called to let them know that my son gave them 50 dollars (two 5 dollars bills & two 20 dollar bills) instead of 20. The food came to $18.25. When I called to let them know that my son is legally blind and did it by mistake because he couldn't see the money that well. The guy on the phone put me on hold and called his driver. He got back on the phone and said my driver said he got four 5 dollar bills. I told him that was not possible because I left my son two 20s and he had two 5s. He also asked me if I was sure he ordered from them. I told him I was holding the receipt from them and he said well my driver said he got four $5 bills. So I told him ok that's fine you have to take your employees word. But I will never order from you again and I will be sure to pass this information along and I hung up. #peoplesuck #takingadvantageofakid #neverorderingfromCheckmateCafeagain #hopetheyenjoythetip #whogivesa30tiponan1825meal read more

Food is as good as any other Greek pizza joint. Their generosity with napkins is an insult. One napkin to a large messy parmesan sub does not cut it. Give a little more respect to your customers read more

I ordered a chicken parm calzone for my family last night. Lots of snow falling but they delivered quickly! The calzone was the best! They don't get much better. Thanks Checkmate! read more

Always consistent. Delivery is easy and fast. Love the jalapeno poppers and their greek chicken salad is awesome- lots of feta! We order at least once a week from here. read more

I have been to many of the pizza and sub shops in Rozzie. Checkmate is unequivocally the best!! Pizza is a thin crust with the right amount of topping that does not overpower the balance of flavor. Subs use a great roll that is the best in Boston in my opinion. They are not soggy like other local shops and have the best cold cuts. The Italian is great but if you want to truly try something phenomenal try the Ultimate sub with sliced pork, ham, cheese, et al on a toasted GARLIC BUTTER roll. It's Insane! I first got their mailer and almost threw it out and noticed free delivery. With all the local delivery restaurants charging money for delivery I figured I would give them a try. I have ordered from them about 20 times and have never been disappointed in the food quality and at a reasonable price!! I have written few reviews but had to tell everyone about this place. Checkmate is a must eat restuaurant!!! read more

We have ordered pizza from here for our church's coffee hour many times, and it's great! They even agreed to open early to get it to us on time! Their pizza is great, as well as the customer service :) read more

We order subs and pizzas from Checkmate on a weekly basis. These guys deserve your business; they are friendly, professional, and always on time with the orders. Try Sarah's special pizza, the buffalo wing calzones, and the turkey and BLT subs. The bread for the subs is delicious, and the turkey is freshly cut--not the packaged turkey you find at the grocery store. read more

I work in Roslindale, and I have been going to Checkmate for many years. This has always been my go-to spot for a quick bite to eat during a lunch break. The food is awesome and there's such an amazing variety to choose from. I have noticed there is new ownership, which made me nervous at first (I didn't want my favorite spot to be ruined), but I have not noticed any difference in quality or taste of the food. Staff has always been friendly to me. This will always be a place I recommend to friends and relatives. read more

BEST BUFFALO CHICKEN CALZONE EVER!!! i have been on a global search for anything that even compares to no avail. I can eat checkmate buff chick calzones all day, err day. Death row last meal son! read more

i had a large steak bomb it cost me 10 bucks to boot it was dry bland and overcooked there was no cheese or peppers in it, when i complained they told me i dont know what im talking about and refused to refund my money needless to say i wont b going back there anytime soon read more

Great takeout and free delivery. Always pleasant. The steak bomb is awesome and the seafood is fresh and reasonably priced. Anything with buffalo chicken is A-One. The specialty pizza are as good or better than anyone in the neighborhood. read more

Moved to Roslindale six months ago, and I've order from Checkmate well over two dozen times during that time period. This place is great for a number of reasons. The quality of service, and the manner in which they greet and treat customers has consistently been great. The staff there are always friendly with both customers and each other. There's always been a good vibe in the place each time I've gone there. It does not pretend to be more than what it is, but the food that I've ordered there has been high quality every time to date. They use fresh roasted turkey for their clubs and other sub sandwiches. The eggplant parmesan is also excellent. I have ordered a number of pizzas. Every one of them was prepared exactly as I ordered. I like their crust and sauce. The service is quick. For a neighborhood pizza, sub, etc. shop, they do what they do really well. read more

I just happen to find out about this place by my mechanic from west roxbury. I called and ordered my favorite chicken parm, and got the very best i ever had. Been a regular there ever since. also their buff chicken calzones are really good. Everything seems to be fresh and " in the store service" its quick and exellent. I used to go to deno's but checkmate will be my final spot. you can never go wrong at checkmate! read more

The food is good and the delivery is dependable. BUT, they don't tell you they add $1.00 when you use a credit card, regardless of total. I have been ordering from them a lot. I won't order anymore because it's dishonest. This fee is NOT on the menu on the yourhomepages website where their menu is posted. Very disappointing about this practice. read more